Copyright Wiley-VCH Verlag GmbH, D Weinheim, Angew. Chem
|
|
- Valerie Lee
- 5 years ago
- Views:
Transcription
1 Copyright Wiley-VCH Verlag GmbH, D Weinheim, Angew. Chem Supporting Information for Salen as Chiral Activator : Anti vs Syn Switchable Diastereoselection in the Enantioselective Addition of Crotyl Bromide to omatic Aldehydes. Marco Bandini, Pier Giorgio Cozzi,* Achille Umani-Ronchi* Angewandte Chemie General: 1 H NMR spectra were recorded on Varian 200 MHz or Varian 300 MHz spectrometers. Chemical Shifts are reported in ppm from tetramethylsilane with the solvent resonance as the internal standard (deuterochloroform: δ 7.27 ppm). Data are reported as follows: chemical shifts, multiplicity (s = singolet, d = douplet, t = triplet, q = quartet, br = broad, m = multiplet), coupling constants (Hz). 13 C NMR spectra were recorded on a Varian 50 MHz or Varian 75 MHz spectrometers with complete proton decoupling. Chemical shifts are reported in ppm from tetramethylsilane with the solvent as the internal standard (deuterochloroform: δ 77.0 ppm). Mass spectra were performed at an ionizing voltage of 70 ev. Chromatographic purification was done with mesh silica gel. Analytical gas chromatography (GC) was performed on a Hewlett-Packard HP 6890 gas chromatograph with a flame ionization detector and split mode capillary injection system, using a Crosslinked 5% PH ME Siloxane (30 m) column or a Megadex5 chiral (25 m) column. Analytical high performance liquid chromatograph (HPLC) was performed on a HP 1090 liquid chromatograph equipped with a variable wavelength UV detector (deuterium lamp nm), using a Daicel Chiralcel TM OD column (0.46 cm I.D. x 25 cm) (Daicel Inc.). HPLC grade isopropanol and hexane were used as the eluting solvents. Elemental analyses were carried out by using a EACE 1110 CHNOS analyzer. All the reactions were carried out under a nitrogen atmosphere in flame-dried glassware using standard inert techniques for introducing reagents and solvents. All the aldehydes were distilled prior to use. All the other commercially obtained reagents were used as received. Anhydrous CH 3 CN were purchased from the Fluka Co. S1
2 Table S1. Influence of the amount of salen on the diastereoselectivity of the chromium catalyzed addition of crotyl bromide to the PhCHO (see Figure 2). Salen (mol%) 8a:9a [a] Syn/Anti ee of 8a [%] [b] ee of 9a [%] [b] 0 12: : : : : : : : [a] Determined by GC analysis of the crude reaction mixture and by 1 H NMR analysis after chromatographic purification. [b] Determined by chiral GC analysis. Table S2. Results of the diastereoselective addition of organohalides to aromatic aldehydes in the presence of CrCl 3 (10 mol%) as the catalyst. RCHO R X [b] Yield Product [%] [a] (Anti:Syn) 7a Cinnamoyl chloride 75 [c] 85:15 7a 3-Bromocyclohexene 55 [c] 99:1 7b Crotyl bromide 82 81:19 7c Crotyl bromide 59 88:12 7d Crotyl bromide 78 79:21 7e Crotyl bromide 80 82:12 7f Crotyl bromide 79 84:16 7g Crotyl bromide 69 73:27 7h Crotyl bromide 31 71:29 [a] Isolated yield after desilylation (HCl/THF) and flash chromatography. [b] Determined by GC analysis of the crude reaction mixture and 1 H NMR analysis after chromatographic purification. [c] Isolated yield after desilylation (Bu 4 NF/THF) and flash chromatography. S2
3 General Procedure A: Catalytic Asymmetric Addition of Stereogenic Organohalides to 7a-h: O H + Hal X "Catalytic System" X >> X CrCl 3 (8 mg,0.05 mmol) and Mn (83 mg, 1.5 mmol) were added to anhydrous CH 3 CN (2 ml) and the mixture was kept for about 5-8 min, then the reaction mixture was stirred until a green-white precipitate was observed. The ligand 1 (55 mg, 0.1 mmol) was introduced followed by dried triethylamine (14 µl, 0.1 mmol) and the resulting brown solution was stirred at room temperature for 1 h. The solution was treated with the appropriate organo halide (0.75 mmol) and the resulting red solution was stirred for 1 h at room temperature. Finally, 7a-h (0.5 mmol) and Me 3 SiCl (95 µl, 0.75 mmol) were added and the mixture was stirred until the complete consumption of the aldehyde (16-24 h, checked by GC). After quenching with a saturated solution of NaHCO 3 (3 ml), the reaction mixture was filtered on a celite bed, and the CH 3 CN was evaporated under reduced pressure. The residue was extracted with Et 2 O (3 x 2 ml) and the organic phases were collected and evaporated under reduced pressure. The oil obtained was dissolved in THF (2 ml) and treated with 0.5 ml of HCl 1N. The mixture was stirred to complete desilylation (checked by TLC). After evaporation of THF, the residue was extracted with Et 2 O. The organic phases were collected, dried over Na 2 SO 4 and concentrated in vacuo to give a brown residue purified by flash chromatography (silica gel, Cyclohexane:Et 2 O). General Procedure B: Synthesis of the O-methyl ether derivatives (12a-g) of 8/9a-g: OMe X X Into a round-bottom flask 2 ml of anhydrous DMF, dry NaH ( mmol) and the alcohol (8a-g/9a-g mixture) ( mmol) was introduced at room temperature. The pale yellow suspension was stirred for 15 min then methyl iodine ( mmol) was added by syringe. The reaction mixture was stirred until complete as monitored by TLC (1-2 h). A saturated solution of NaHCO 3 (2 ml) and 2 ml of Et 2 O were then added, and the organic layer was separated, washed with HCl 1N (2 ml) and brine and dried over Na 2 SO 4. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure. The crude reaction mixture was purified by flash chromatography (silica gel, Cyclohexane:Et 2 O). The addition of the 10 mol% excess of salen just before the crotyl bromide afforded the product in comparable level of stereoselectivity. S3
4 2-Methyl-1-phenyl-3-en-1-ol (8a): General procedure A followed employing 50 µl of 7a (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (15% Et 2 O in cyclohexane) gave 45 mg (56%) of the title compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 83:17. OMe (1-Methoxy-2-methyl-but-3-enyl)-benzene (12a): General procedure B followed employing 45 mg of 8a (0.28 mmol). Purification by flash chromatography (5% Et 2 O in cyclohexane) gave 48 mg (>98%) of the title compound (colorless oil). Separation of the stereoisomers by chiral GC (Megadex5 column, 25 m, flow rate carrier 70 Kpa, method: 80 C isoterm, T r : 21.0 (1S,2R), 22.0 (1R,2S), 24.6 (1R,2R) and 25.1 (1S,2S) min) provided the diastereomeric ratio syn:anti 83:17 and the enantiomeric ratios: (syn 1R,2S ):(syn 1S,2R ) = 94.5:5.5 (89% ee), (anti 1S,2S ):(anti 1R,2R ) = 68.0:32.0 (36% ee). MS (EI, 70 ev): m/z 130, 128, 121, 115, 105, 91, 77, 51; 1 H NMR (200 MHz, CDCl 3 ) (syn isomer): δ (m, 5H), (m, 1H), (m, 2H), 3.95 (d, J = 9.00 Hz, 1H), 3.23 (s, 3H), 2.52 (m, 1H), 1.07 (d, J = 6.84 Hz, 3H); (anti isomer, diagnostic signals): δ 3.92 (d, J = 7.42 Hz, 1H), 2.54 (q, J = 7.24 Hz, 1H), 0.85 (d, J = 6.92 Hz, 3H); 13 C NMR (75 MHz, CDCl 3 ) (syn isomer): δ 140.5, 138.1, 127.9, 127.4, 127.3, 114.4, 87.8, 57.0, 44.3, 15.5; (anti isomer, diagnostic signals): δ 114.2, 88.1, 16.4; Anal. Calcd for C 12 H 16 O: C, 81.77; H, 9.15; O, Found: C, 81.89; H, 9.10; O, Methyl-1-p-tolyl-but-3-en-1-ol (8b): General procedure A followed employing 59 µl of 7b (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (20% Et Me 2 O in cyclohexane) gave 42 mg (48%) of the title compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 74:26. Me OMe 1-(1-Methoxy-2-methyl-but-3-enyl)-benzene (12b): General procedure B followed employing 42 mg of 8b (0.24 mmol). Purification by flash chromatography (5% Et 2 O in cyclohexane) gave 45 mg (>98%) of the title compound (colorless oil). S4
5 Separation of the stereoisomers by chiral GC (Megadex5 column, 25 m, flow rate carrier 70 Kpa, method: 80 C isoterm, T r : 40.2 (1S,2R), 41.5 (1R,2S), 40.7 (1R,2R) and 50.5 (1S,2S) min) provided the diastereomeric ratio syn:anti 74:26 and the enantiomeric ratios: (syn 1R,2S ):(syn 1S,2R ) = 92.5:7.5 (85% ee), (anti 1S,2S ):(anti 1R,2R ) = 60.0:40.0 (20% ee). MS (EI, 70 ev): m/z 159, 135, 119, 105, 91, 65, 51; 1 H NMR (300 MHz, CDCl 3 ) (syn isomer): δ (m, 4H), (m, 1H), 4.95 (dd, J 1 = 5.7 Hz, J 2 = 1.4 Hz, 1H), 4.90 (d, J = 1.4 Hz, 1H), 3.93 (d, J = 6.60 Hz, 1H), 3.21 (s, 3H), (m, 1H), 2.36 (s, 3H), 1.02 (d, J = 6.60 Hz, 3H); (anti isomer, diagnostic signals): δ 3.89 (d, J = 7.50 Hz, 1H), 3.19 (s, 3H), 0.87 (d, J = 6.90 Hz, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ 140.5, 137.3, 136.9, 128.6, 127.4, 114.3, 87.6, 56.9, 44.2, 21.2, 15.5; (anti isomer, diagnostic signals): δ 114.1, 88.0, 44.3, 16.4; Anal. Calcd for C 13 H 18 O: C, 82.06; H, 9.53; O, Found: C, 82.00; H, 9.46; O, (4-Fluoro-phenyl)-2-methyl-1-but-3-en-1-ol (8c): General procedure A followed employing 68 µl of 7c (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (15% Et 2 O in cyclohexane) gave 48 mg (53%) of the title F compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 74:26. OMe 1-Fluoro-4-(1-methoxy-2-methyl-but-3-enyl)-benzene (12c): General procedure B followed employing 48 mg of 8c (0.25 mmol). Purification by flash chromatography (5% Et 2 O in cyclohexane) gave 51 mg (>98%) of the title compound (colorless oil). F Separation of the stereoisomers by chiral GC (Megadex5 column, 25 m, flow rate carrier 70 Kpa, method: 110 C isoterm, T r : 5.1 (1S,2R), 5.3 (1R,2S), 5.8 (1R,2R) and 6.0 (1S,2S) min) provided the diastereomeric ratio syn:anti 74:26 and the enantiomeric ratios: (syn 1R,2S ): (syn 1S,2R ) = 95.0:5.0 (90% ee), (anti 1S,2S ):(anti 1R,2R ) = 64.5:36.5 (27% ee). MS (EI, 70 ev): m/z 146, 140, 139, 133, 123, 109, 95, 91, 75, 51; 1 H NMR (300 MHz, CDCl 3 ) (syn isomer): δ (m, 2H), (m, 2H), 5.65 (ddd, J Hz, J 2 = Hz, J 3 = Hz, 1H), (m, 2H), 3.93 (d, J = 6.60 Hz, 1H), 3.21 (s, 3H), 2.50 (q, J = 7.20 Hz, 1H), 1.05 (d, J = 6.90 Hz, 3H); (anti isomer, diagnostic signals): δ 3.92 (d, J = 5.40 Hz, 1H), 3.19 (s, 3H), 0.84 (d, J = 6.90 Hz, 3H); 13 C NMR (50 MHz, CDCl 3 ): δ 159.4, 140.2, 129.1, 128.9, 115.1, 114.8, 87.2, 56.9, 44.3, 15.6; (anti isomer, diagnostic signals): δ140.9, 115.2, 114.6, 87.5, Anal. Calcd for C 12 H 15 FO: C, 74.20; H, 7.78; O, Found: C, 74.32; H, 7.74; O, (4-Chloro-phenyl)-2-methyl-1-but-3-en-1-ol (8d): General procedure A followed employing 70 mg of 7d (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (20% Et 2 O in cyclohexane) gave 45 mg (46%) of the title Cl compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 61:39. S5
6 OMe 1-Chloro-4-(1-methoxy-2-methyl-but-3-enyl)-benzene (12d): General procedure B followed employing 45 mg of 8d (0.23 mmol). Purification by flash chromatography (5% Et 2 O in cyclohexane) gave 47 mg (>98%) of the title compound (colorless oil). Cl Separation of the stereoisomers by chiral GC (Megadex5 column, 25 m, flow rate carrier 70 Kpa, method: 100 C isoterm, T r : 31.2 (1S,2R), 32.6 (1R,2S), 36.3 (1R,2R) and 38.4 (1S,2S) min) provided the diastereomeric ratio syn:anti 61:39 and the enantiomeric ratios: (syn 1R,2S ):(syn 1S,2R ) = 91.0:9.0 (82% ee), (anti 1S,2S ):(anti 1R,2R ) = 62.0:38.0 (24% ee). MS (EI, 70 ev): m/z 157, 155, 139, 110, 91, 51; 1 H NMR (200 MHz, CDCl 3 ) (syn isomer): δ (m, 2H), (m, 2H), (m, 1H), (m, 2H), 3.91 (d, J = 6.30 Hz, 1H), 3.20 (s, 3H), 2.46 (q, J = 6.88 Hz, 1H), 1.04 (d, J = 6.76 Hz, 3H); (anti isomer, diagnostic signals): δ 5.84 (ddd, J 1 = 7.42 Hz, J 2 = Hz, J 3 = Hz, 1H), (m, 2H), 3.91 (d, J = 6.96 Hz, 1H), 0.85 (d, J = 6.92 Hz, 3H); 13 C NMR (50 MHz, CDCl 3 ) (syn isomer): δ 141.0, 140.6, 131.1, 129.2, 121.3, 114.7, 87.2, 57.1, 41.2, 15.4; (anti isomer, diagnostic signals): δ 140.0, 139.5, 131.2, 129.2, 121.2, 87.5, 44.2, 16.2; Anal. Calcd for C 12 H 15 ClO: C, 68.40; H, 7.18; O, Found: C, 68.51; H, 7.14; O, (4-Bromo-phenyl)-2-methyl-but-3-en-1-ol (8e): General procedure A followed employing 92 mg of 7e (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (20% Et 2 O in cyclohexane) gave 52 mg (43%) of the title Br compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 72:28. OMe 1-Bromo-4-(1-methoxy-2-methyl-but-3-enyl)-benzene (12e): General procedure B followed employing 52 mg of 8e (0.22 mmol). Purification by flash chromatography (5% Et 2 O in cyclohexane) gave 54 mg (>98%) of the title compound (colorless oil). Br Separation of the stereoisomers by chiral GC (Megadex5 column, 25 m, flow rate carrier 70 Kpa, method: 110 C for 28 min, 3 C/min to 130 C for 20 min, T r : 29.8 (1S,2R), 31.0 (1R,2S), 31.8 (1R,2R) and 32.5 (1S,2S) min) provided the diastereomeric ratio syn:anti 72:28 and the enantiomeric ratios: (syn 1R,2S ):(syn 1S,2R ) = 91.0:9.0 (82% ee), (anti 1R,2R ):(anti 1S,2S ) = 64.0:36.0 (28% ee). MS (EI, 70 ev): m/z 201, 199, 187, 185, 159, 157, 120, 94, 92, 51; 1 H NMR (200 MHz, CDCl 3 ) (syn isomer): δ (m, 2H), (m, 2H), (m, 1H), (m, 2H), 3.92 (d, J = 6.30 Hz, 1H), 3.21 (s, 3H), 2.47 (q, J 1 = 6.60 Hz, 1H), 1.04 (d, J = 6.80, 3H); (anti isomer, diagnostic signals): δ 3.90 (d, J = 6.88 Hz, 1H), 0.86 (d, J = 6.88, 3H); 13 C NMR (50 MHz, CDCl 3 ): δ 140.6, 139.5, 131.1, 129.2, 121.2, 114.9, 87.2, 57.1, 44.2, 15.4; (anti isomer, diagnostic signals): δ 140.0, 131.2, 128.5, 114.7, 87.5, 56.7, 41.2, 16.2; Anal. Calcd for C 12 H 15 BrO: C, 56.49; H, 5.93; O, Found: C, 56.40; H, 5.88; O, Br 1-(3-Bromo-phenyl)-2-methyl-but-3-en-1-ol (8f): General procedure A followed employing 58 µl of 7f (0.50 mmol) and trcrotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (20% Et 2 O in cyclohexane) gave 59 mg (49%) of the title compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, S6
7 method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 66:34. Br Ph OAc (S)-(+)-Acetoxy-phenyl-acetic acid 1-(3-bromo-phenyl)-2-methyl-but-3-enyl ester O O (13): The O-ester was synthesized by adding dropwise the mandelic chloride (1.2 eq.) to a solution of 8f (1eq.), DMAP (0.1 eq), and pyridine (few drops) in anhydrous CH 2 Cl 2 at 0 C. The enantiomeric excess was determination by 1 H NMR analysis. Diagnostic signals (300 MHz, CDCl 3 ) : δ syn 0.79 (d, J = 6.90 Hz, 3H), syn 1.02 (d, J = 6.90 Hz, 3H), anti 0.74 (d, J = 6.90 Hz, 3H), anti 0.91 (d, J = 6.90 Hz, 3H). Ee syn = 70%, ee anti = 43%; Anal. Calcd for C 21 H 21 BrO 4 : C, 60.44; H, 5.07; O, Found: C, 60.32; H, 5.03; O, (4-Methoxy-phenyl)-2-methyl-but-3-en-1-ol (8g): General procedure A followed employing 57 µl of 7g (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (20% Et 2 O in cyclohexane) gave 50 mg (52%) of the title MeO compound (pale yellow oil). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 60:40. OMe 1-Methoxy-4-(1-methoxy-2-methyl-but-3-enyl)-benzene (12g): General procedure B followed employing 50 mg of 8g (0.26 mmol). Purification by flash chromatography (5% Et 2 O in cyclohexane) gave 53 mg (>98%) of the title compound (colorless oil). MeO Separation of the stereoisomers by chiral GC (Megadex5 column, 25 m, flow rate carrier 70 Kpa, method: X C isoterm, T r : 47.0 (1S,2R), 47.8 (1R,2S), 54.2 (1R,2R), 56.5 (1S,2S) min) provided the diastereomeric ratio syn:anti 60:40 and the enantiomeric ratios: (syn 1R,2S ):(syn 1S,2R ) = 79:21 (58% ee), (anti 1S,2S ):(anti 1R,2R ) = 57.5:42.5 (15% ee). MS (EI, 70 ev): m/z 151, 136, 109, 91, 77, 65; 1 H NMR (200 MHz, CDCl 3 ) (syn isomer): δ (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 1H), 3.82 (s, 3H), 3.19 (s, 3H), (m, 1H), 1.05 (d, J = 6.68 Hz, 3H); (anti isomer, diagnostic signals): δ 3.88 (m, 1H), 3.18 (s, 3H), 0.83 (d, J = 6.7 Hz, 3H); 13 C NMR (50 MHz, CDCl 3 ): δ 140.6, 128.6, 127.9, 114.4, 113.3, 87.4, 56.7, 55.2, 44.2, 15.6; (anti isomer, diagnostic signals): δ 141.5, 127.3, 114.2, 113.5, 87.7, 44.3, 16.4; Anal. Calcd for C 13 H 18 O 2 : C, 75.69; H, 8.80; O, Found: C, 75.77; H, 8.74; O, Ph 1-Biphenyl-4-yl-2-methyl-but-3-en-1-ol (8h): General procedure A followed employing 91 mg of 7h (0.50 mmol) and crotyl bromide 77 µl (0.75 mmol). Purification by flash chromatography (15% Et 2 O in cyclohexane) gave 56 mg (47%) of the title compound. S7
8 Separation of the stereoisomers by chiral HPLC (Daicel Chiralcel TM OD column, flow rate 0.5 ml/min, 2% ipr, 98% hexane, T r : 22.8 (1S,2S), 23.6 (1R,2S), 24.8 (1R,2R) and 26.4 (1S,2R) min) provided the diastereomeric ratio syn:anti 71:29 and the enantiomeric ratios: (syn 1R,2S ):(syn 1S,2R ) = 92.0:8.0 (84% ee), (anti 1S,2S ):(anti 1R,2R ) = 58.0:42.0 (16% ee). 1 H NMR (300 MHz, CDCl 3 ) (syn isomer): δ (m, 4H), (m, 5H), (m, 1H), (m, 2H), 4.69 (br, 1H), (m, 1H), 1.07 (d, J = 6.90 Hz, 3H); (anti isomer, diagnostic signals): δ 4.20 (d, J = 8.10 Hz, 1H), 0.93 (d, J = 6.90 Hz, 3H); 13 C NMR (50 MHz, CDCl 3 ): δ 140.8, 140.2, 130.8, 129.0, 128.7, 127.6, 127.0, 126.9, 126.7, 115.6, 77.0, 44.6, 14.0; (anti isomer, diagnostic signals): δ 141.6, 140.6, 116.9, 46.2, 16.5; Anal. Calcd for C 17 H 18 O: C, 85.67; H, 7.61; O, Found: C, 85.52; H, 7.54; O, ,2-Diphenyl-but-3-en-1-ol (14): General procedure A followed employing 90 mg of 7a (0.5 mmol). and cinnamoyl chloride 72 µl (0.75 mmol) Purification by flash chromatography (15% Et 2 O in cyclohexane) gave 81 mg (72%) of the title compound (white solid). Separation of the diastereoisomers (trimethylsilyl ether derivatives) by GC (Crosslinked 5% PH ME Siloxane column, 30 m, flow rate 15 ml/min, method: 50 C for 2 min, 10 C/min to 250 C for 15 min, T r : (anti) and (syn) min) provided the diastereomeric ratio syn:anti 75:25. Separation of the stereoisomers by chiral HPLC (Daicel Chiralcel TM OD column, flow rate 0.5 ml/min, 2% ipr, 98% hexane, T r : 31.5 (<anti), 33.3 (>anti), 34.4 (<syn) and 36.1 (>syn) min) provided the diastereomeric ratio syn:anti 75:25 and the enantiomeric ratios: syn = 93.0:7.0 (86% ee), anti = 63.0:37.0 (26% ee). 1 H NMR (300 MHz, CDCl 3 ) (syn isomer): δ (m, 9H), 7.05 (d, J = 6.90 Hz, 1H), 5.90 (ddd, J 1 = 7.80 Hz, J 2 = Hz, J 3 = Hz, 1H), 5.00 (dd, J 1 = 0.60 Hz, J 2 = 9.60 Hz, 1H), (m, 2H), 3.64 (t, J = 8.10 Hz, 1H), 1.93 (d, J = 3.00 Hz, 1H); (anti isomer, diagnostic signals): 4.92 (d, J = 3.00 Hz, 1H), 3.55 (t, J = 8.40 Hz, 1H), 2.29 (d, J = 2.40 Hz, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ 141.5, 140.6, 140.2, 128.7, 127.2, 127.0, 126.9, 126.7, 116.9, 115.6, 76.4, 44.8, 13.9; Anal. Calcd for C 16 H 16 O: C, 85.68; H, 7.19; O, Found: C, 85.77; H, 7.15; O, Cyclohex-2-enyl-phenyl-methanol (15): General procedure A followed employing 50 µl of 7a (0.5 mmol) and 3-bromocyclohexene 86 µl (0.75 mmol). Purification by flash chromatography (20% Et 2 O in cyclohexane) gave 21 mg (22%) of the title compound. Separation of the stereoisomers by chiral HPLC (Daicel Chiralcel TM OD column, flow rate 0.5 ml/min, 5% ipr, 95% hexane, T r : 13.9 (>anti), 14.5 (<syn), 16.0 (>syn) and 17.0 (<anti) min) provided the diastereomeric ratio syn:anti 75:25 and the enantiomeric ratios: syn = 76.0:24.0 (52% ee), anti = 50.0:50.0. MS (EI, 70 ev): m/z 128, 107, 81, 79, 51; 1 H NMR (200 MHz, CDCl 3 ) (syn isomer): δ (m, 5H), (m, 2H), 4.59 (dd, J 1 = 6.40 Hz, J 2 = 3.38 Hz, 1H), 2.51 (br, 2H), (m, 6H); (anti isomer): δ (m, 2H), 4.48 (dd, J 1 = 6.60 Hz, J 2 = 1.10 Hz, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ 142.2, 130.4, 128.2, 126.4, 77.2, 43.0, 25.3, 23.8, 21.1; (anti isomer): δ 77.7, 42.9, 21.5; Anal. Calcd for C 13 H 16 O: C, 82.94; H, 8.57; O, Found: C, 82.88; H, 8.50; O, S8
Supporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Enantioselective Cu-catalyzed 1,4-Addition of Various Grignard Reagents to Cyclohexenone using Taddol-derived Phosphine-Phosphite
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Enantioselective Rhodium-catalyzed Addition of Arylboronic Acids to α-ketoesters Hai-Feng Duan, Jian-Hua Xie, Xiang-Chen Qiao, Li-Xin Wang,
More informationSupporting information
Supporting information Diversity Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-aminophenol aminophenol (IAP)-Ni Catalyzed Michael/Henry
More informationElectronic Supplementary Information. Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of
Electronic Supplementary Information Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of Allylic Alcohols: An Effective and Enantioselective Approach to α Quaternary β Fluoro
More informationEnantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction P. Veeraraghavan Ramachandran* and Prem B. Chanda Department of Chemistry, Purdue
More informationSupporting Information. for. Pd-catalyzed decarboxylative Heck vinylation of. 2-nitro-benzoates in the presence of CuF 2
Supporting Information for Pd-catalyzed decarboxylative Heck vinylation of 2-nitro-benzoates in the presence of CuF 2 Lukas J. Gooßen*, Bettina Zimmermann, Thomas Knauber Address: Department of Chemistry,
More information# Supplementary Material (ESI) for Chemical Communications # This journal is The Royal Society of Chemistry 2005
Electronic Supplementary Information for: (Z)-Selective cross-dimerization of arylacetylenes with silylacetylenes catalyzed by vinylideneruthenium complexes Hiroyuki Katayama,* Hiroshi Yari, Masaki Tanaka,
More informationLewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines
Supporting Information for Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines Yingle Liu a, Jiawang Liu
More informationPreparation of Stable Aziridinium Ions and Their Ring Openings
Supplementary Information Preparation of Stable Aziridinium Ions and Their Ring Openings Yongeun Kim a Hyun-Joon Ha*, a Sae Young Yun b and Won Koo Lee,*,b a Department of Chemistry and Protein Research
More informationSupporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylin
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylindoles Wei-Li Chen, Si-Yi Wu, Xue-Ling Mo, Liu-Xu Wei,
More informationSupporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
More informationMasatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa,
More informationSupplementary Materials Contents
Supplementary Materials Contents Supporting information... S1 1. General Information & Materials... S2 2. General Procedure for ptimization of Amidation of Aryl Bromides with Copper/,-Dimethylglycine Catalytic
More informationSupporting Information
J. Am. Chem. Soc. Supporting Information S 1 Enantioselective rganocatalytic Indole Alkylations. Design of a New and Highly Effective Chiral Amine for Iminium Catalysis. Joel F. Austin and David W. C.
More informationAsymmetric organocatalytic diboration of alkenes
Asymmetric organocatalytic diboration of alkenes Amadeu Bonet, a Cristina Solé, Henrik Gulyás,* Elena Fernández* a Dept. Química Física i Inorgànica, University Rovira i Virgili, C/Marcel lí Domingo s/n,
More informationp-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
More informationSupporting Information. for. Access to pyrrolo-pyridines by gold-catalyzed. hydroarylation of pyrroles tethered to terminal alkynes
Supporting Information for Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Elena Borsini 1, Gianluigi Broggini* 1, Andrea Fasana 1, Chiara Baldassarri
More informationDivergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
More informationSupporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
More informationStereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines
Stereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines Toni Moragas Solá, a Ian Churcher, b William Lewis a and Robert A. Stockman* a Supplementary Information
More informationSupporting Materials. Experimental Section. internal standard TMS (0 ppm). The peak patterns are indicated as follows: s, singlet; d,
CuBr-Catalyzed Efficient Alkynylation of sp 3 C-H Bonds Adjacent to a itrogen Atom Zhiping Li and Chao-Jun Li* Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Organocatalytic Asymmetric Sulfa-Michael Addition to α,β- Unsaturated Ketones Paolo Ricci, Armando Carlone, Giuseppe
More informationUniversity of Groningen
University of Groningen Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates Piarulli, Umberto; Claverie, Christelle; Daubos, Philippe; Gennari,
More informationSupporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
More informationRegioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, Chunxiang Kuang,* Department of Chemistry, Tongji University,
More informationSupporting Information
Supporting Information Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt Prosenjit Daw, Yehoshoa Ben-David, and David Milstein* Department
More informationRuthenium-Catalyzed C H Oxygenation on Aryl Weinreb Amides
Supporting Information Ruthenium-Catalyzed C H xygenation on Aryl Weinreb Amides Fanzhi Yang and Lutz Ackermann* Institut für rganische und Biomolekulare Chemie Georg-August-Universität Tammannstrasse
More informationSupporting Information
Zinc-Mediated Addition of Diethyl Bromomalonate to Alkynes for the Cascade Reaction towards Polysubstituted Pyranones and Tetracarbonyl Derivatives Anne Miersch, Klaus Harms, and Gerhard Hilt* Fachbereich
More informationZinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides
Supporting information for Zinc Chloride Promoted Formal xidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides Marinus Bouma, Géraldine Masson* and Jieping Zhu* Institut de Chimie des
More informationNitro-Grela-type complexes containing iodides. robust and selective catalysts for olefin metathesis
Supporting Information for Nitro-Grela-type complexes containing iodides robust and selective catalysts for olefin metathesis under challenging conditions. Andrzej Tracz, 1,2 Mateusz Matczak, 1 Katarzyna
More informationStudent Handout. This experiment allows you to explore the properties of chiral molecules. You have
Student Handout This experiment allows you to explore the properties of chiral molecules. You have learned that some compounds exist as enantiomers non-identical mirror images, such as your left and right
More informationSupporting Information. Recyclable hypervalent-iodine-mediated solid-phase peptide
Supporting Information Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis Dan Liu, Ya-Li Guo, Jin Qu and Chi Zhang* for Address: State Key Laboratory of Elemento-Organic
More informationEthyl 2-hydroxy-4-methyl-1-((prop-2-yn-1-yloxy)methyl)cyclohex-3-enecarboxylate (16):
General methods: 1 H NMR and 13 C NMR spectra were recorded in CDCl 3 or CDCl3 and CCl 4 as solvent on 300 MHz or 500 MHz spectrometer at ambient temperature. The coupling constant J is given in Hz. The
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2016 Supporting Information Fangyi Li, Changgui Zhao, and Jian Wang* Department of Pharmacology
More informationSupporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
More informationAll chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without
Supplemental Data Alexander et al. Experimental Procedures General Methods for Inhibitor Synthesis All chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without further purification,
More informationNovel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine. Resistant Breast Cancer Therapeutics
Page 11 of 32 Cancer Chemotherapy and Pharmacology Novel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine Resistant Breast Cancer Therapeutics James W. Antoon, Jiawang Liu, Adharsh P. Ponnapakkam,
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationSupporting Information
Supporting Information Unconventional Passerini Reaction towards α-aminoxyamides Ajay L. Chandgude, Alexander Dömling* Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV
More informationIron-Catalyzed Alkylation of Alkenyl Grignard Reagents
Supporting Information for Iron-Catalyzed Alkylation of Alkenyl Grignard Reagents Gérard Cahiez,* Christophe Duplais and Alban Moyeux Laboratoire de Synthèse Organique Sélective et de Chimie Organométallique
More informationElectronic Supplementary Information
Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun
More informationSolid Phase Peptide Synthesis (SPPS) and Solid Phase. Fragment Coupling (SPFC) Mediated by Isonitriles
Solid Phase Peptide Synthesis (SPPS) and Solid Phase Fragment Coupling (SPFC) Mediated by Isonitriles Ting Wang a and Samuel J. Danishefsky a,b,* alaboratory for Bioorganic Chemistry, Sloan- Kettering
More informationRameshwar Prasad Pandit and Yong Rok Lee * School of Chemical Engineering, Yeungnam University, Gyeongsan , Korea
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Novel ne-pot Synthesis of Diverse γ,δ-unsaturated β-ketoesters by Thermal
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Supporting Information General. NMR spectra for identification of intermediates and final compoundswere recorded
More informationImproved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides
Albaneze-Walker et al S-1 Improved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides Jennifer Albaneze-Walker*, Charles Bazaral, Tanya Leavey, Peter G. Dormer, and Jerry A. Murry Department
More informationmm C3a. 1 mm C3a Time (s) C5a. C3a. Blank. 10 mm Time (s) Time (s)
125 I-C5a (cpm) Fluorescnece Em 520nm a 4000 3000 2000 1000 c 0 5000 4000 3000 2000 Blank C5a C3a 6 0.3 mm C3a 7 9 10 11 12 13 15 16 0.3 mm C5a 0 300 600 900 1200 Time (s) 17 Fluorescnece Em 520nm Fluorescnece
More informationSupporting Information
Supporting Information B(C 6 F 5 ) 3 -catalyzed Regioselective Deuteration of Electronrich Aromatic and Heteroaromatic compounds Wu Li, Ming-Ming Wang, Yuya Hu and Thomas Werner* Leibniz-Institute of Catalysis
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Exploiting the Ring Strain in Bicyclo[2.2.1]heptane Systems for the Stereoselective Preparation of Highly Functionalized Cyclopentene, Dihydrofuran, Pyrroline and Pyrrolidine Scaffolds
More informationSimple copper/tempo catalyzed aerobic dehydrogenation. of benzylic amines and anilines
Simple copper/tempo catalyzed aerobic dehydrogenation of benzylic amines and anilines Zhenzhong Hu and Francesca M. Kerton,* Department of Chemistry, Memorial University of Newfoundland, St. John s, NL,
More informationAllenylphosphine oxides as simple scaffolds for. phosphinoylindoles and phosphinoylisocoumarins
Supporting Information for Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins G. Gangadhararao, Ramesh Kotikalapudi, M. Nagarjuna Reddy and K. C. Kumara Swamy*
More informationSupporting Information
Supporting Information Developing novel activity-based fluorescent probes that target different classes of proteases Qing Zhu, Aparna Girish, Souvik Chattopadhaya and Shao Q Yao * Departments of Chemistry
More informationDirect ortho-c H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-palladacycle
Direct ortho-c H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-palladacycle Kun Guo, Xiaolan Chen, Mingyu Guan, and Yingsheng Zhao* Key Laboratory of Organic Synthesis of
More informationCu-Catalyzed Direct C6-Arylation of Indoles
Cu-Catalyzed Direct C6-Arylation of Indoles (Supporting Information) Youqing Yang, Ruirui Li, Yue Zhao, Dongbing Zhao, and Zhuangzhi Shi*, State Key Laboratory of Coordination Chemistry, Collaborative
More informationSchwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins
Electronic Supplementary Information (ESI) Schwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins A. Ulikowski and B. Furman* Institute of Organic Chemistry, Polish
More informationManganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature
Supplementary Information Manganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature Weili Si 1, Xuan Zhang 1, Shirong Lu 1, Takeshi Yasuda
More informationSupplementary Information Titles
CRRESPNDING AUTHR: MS NUMBER: MS TYPE: Fasan NCHEMB-BC080803093A Brief Communication Supplementary Information Titles Journal: Nature Chemical Biology Article Title: Corresponding Author: Supplementary
More informationDirect Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source
Direct Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source Xuesong Wu, Yan Zhao, and Haibo Ge* Table of Contents General Information...
More informationHighly enantioselective tandem enzyme-organocatalyst crossed aldol reactions. with acetaldehyde in deep-eutectic-solvents.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Highly enantioselective tandem enzyme-organocatalyst crossed aldol reactions with acetaldehyde
More informationAnalysis of fatty acid metabolism using Click-Chemistry and HPLC-MS
Analysis of fatty acid metabolism using Click-Chemistry and HPLC-MS Alexander J. Pérez and Helge B. Bode -Supporting Information- Contents Experimental section Supplementary figures NMR spectra Page S2
More informationPalladium(II)-Catalyzed Cross-Coupling of Simple Alkenes with Acrylates: A Direct Approach to 1,3-Dienes through C H Activation
1 Palladium(II)-Catalyzed Cross-Coupling of Simple Alkenes with Acrylates: A Direct Approach to 1,3-Dienes through C H Activation Zhen-Kang Wen, Yun-He Xu* and Teck-Peng Loh* Division of Chemistry and
More informationSupporting Information
Investigation of self-immolative linkers in the design of hydrogen peroxide metalloprotein inhibitors Jody L. Major Jourden, Kevin B. Daniel, and Seth M. Cohen* Department of Chemistry and Biochemistry,
More informationSupporting Information. Ruthenium(II)-Catalyzed C H Alkynylation of Weakly-Coordinating Benzoic Acids. Ruhuai Mei, Shou-Kun Zhang, and Lutz Ackermann*
Supporting Information Ruthenium(II)-Catalyzed C H Alkynylation of Weakly-Coordinating Benzoic Acids Ruhuai Mei, Shou-Kun Zhang, and Lutz Ackermann* Institut für Organische und Biomolekulare Chemie, Georg-August-Universität
More informationOrvinols with Mixed Kappa/Mu Opioid Receptor Agonist Activity
Supporting Information Orvinols with Mixed Kappa/Mu Opioid Receptor Agonist Activity Greedy, Benjamin M.; Bradbury, Faye.; Thomas, Mark P.; Grivas, Konstantinos; Cami-Kobeci, Gerta; Archambeau, Ashley.;
More informationSupporting Information
Supporting Information Cobalt-Catalyzed Carbonylation of C(sp 2 )-H Bonds with Azodicarboxylate as the Carbonyl Source Jiabin Ni,, Jie Li,,š Zhoulong Fan,, and Ao Zhang *,,,š CAS Key Laboratory of Receptor
More informationPreparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF
Supporting information Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF Otome E. Okoromoba, a Gerald B. Hammond, a, * Bo Xu b, * a Department
More informationSupporting Information
Supporting Information Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines Sayantani Das, Nilanjana Majumdar, Chandra Kanta De, Dipti Sankar Kundu, Arno Döhring,
More informationSUPPORTING INFORMATION. Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S
1 SUPPORTING INFORMATION Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by Chan-Lam Cross-Coupling Reaction SATYA KARUNA PULAKHANDAM a, NARESH KUMAR KATARI
More informationSupporting Information. Stereoselective synthesis of trans-fused iridoid. lactones and their identification in the parasitoid
Supporting Information for Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones Nicole Zimmermann,
More informationSupporting Information. for. Synthesis of dye/fluorescent functionalized. dendrons based on cyclotriphosphazene
Supporting Information for Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene Aurélien Hameau 1,2, Sabine Fuchs 1,2, Régis Laurent 1,2, Jean-Pierre Majoral* 1,2 and Anne-Marie
More informationSynthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice
Supporting Information Rec. Nat. Prod. 9:4 (2015) 561-566 Synthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice Anita Mahapatra 1*, Purvi Shah 1, Mehul Jivrajani
More informationSupporting Information. Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
Supporting Information Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition Shan Xu, Juyou Lu and Hua Fu* Key Laboratory of Bioorganic Phosphorus Chemistry and
More informationSupporting Information. Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as
Supporting Information Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as CO Source Guanglong Sun,,, Xue Lv,,, Yinan Zhang, Min Lei,*,, and Lihong Hu*, Jiangsu Key Laboratory for Functional
More informationChristophe Lincheneau, Bernard Jean-Denis and Thorfinnur Gunnlaugsson* Electronic Supplementary Information
Self-assembly formation of mechanically interlocked [2]- and [3]catenanes using lanthanide ion [Eu(III)] templation and ring closing metathesis reactions Christophe Lincheneau, Bernard Jean-Denis and Thorfinnur
More informationCatalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds Cui-Feng Yang, Jian-Yong Wang and Shi-Kai Tian* Joint Laboratory of Green
More informationPyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles. Supporting Information
Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles Vinaykumar Kanchupalli, Desna Joseph and Sreenivas Katukojvala* Department of Chemistry, Indian Institute
More informationSupporting Information. for. Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated. photochemical N O bond-forming
Supporting Information for Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated photochemical N O bond-forming cyclization of 2-azidobenzoic acids Daria Yu. Dzhons and Andrei V. Budruev* Address:
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 6951 Weinheim, 2008 COMMUNICATION Copper or Iron Catalysed Arylation of Phenols from respectively Aryl Chlorides and Aryl Iodides Ning
More informationDevelopment of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells
Supporting Information for Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells Sasa Zhu, Weiying Lin,* Lin Yuan State Key Laboratory of Chemo/Biosensing
More informationElectronic Supplementary Material
Electronic Supplementary Material PAMAM Dendrimers Bearing Electron-Donating Chromophores: Fluorescence and Electrochemical Properties Bing-BingWang a, Xin Zhang a, Ling Yang a, Xin-Ru Jia* a, Yan Ji a,
More informationDesign, Synthesis and Evaluation of a Series of Novel Benzocyclobutene Derivatives as General Anesthetics
Design, Synthesis and Evaluation of a Series of Novel Benzocyclobutene Derivatives as General Anesthetics Chen Zhang*, Fangqiong Li, Yan Yu, Anbang Huang, Ping He, Ming Lei, Jianmin Wang, Longbin Huang,
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Gold Catalysis: The Phenol Synthesis in the Presence of Functional Groups A. Stephen K. Hashmi, Jan P. Weyrauch,
More informationSupporting Information. An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization
Supporting Information An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization Michiaki, Kawahara, Atsushi Nishida, Masako Nakagawa* Faculty of Pharmaceutical
More informationAn Unusual Glycosylation Product from a Partially Protected Fucosyl Donor. under Silver Triflate activation conditions. Supporting information
An Unusual Glycosylation Product from a Partially Protected Fucosyl Donor under Silver Triflate activation conditions Robin Daly a and Eoin M. Scanlan* a e-mail: eoin.scanlan@tcd.ie a Trinity Biomedical
More informationEfficient and green, microwave assisted synthesis of haloalkylphosphonates via Michaelis-Arbuzov reaction
ELECTRONIC SUPPORTING INFORMATION Efficient and green, microwave assisted synthesis of haloalkylphosphonates via Michaelis-Arbuzov reaction Petr Jansa, Antonín Holý, Martin Dračinský, Ondřej Baszczyňski,
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationNovel Aldosterone Synthase Inhibitors with Extended Carbocyclic Skeleton by a Combined Ligand-Based and Structure-Based Drug Design Approach
Supporting Information Novel Aldosterone Synthase Inhibitors with Extended Carbocyclic Skeleton by a Combined Ligand-Based and Structure-Based Drug Design Approach Simon Lucas, Ralf Heim, Matthias Negri,
More informationSUPPLEMENTARY INFORMATION
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 218 SUPPLEMENTARY INFORMATION Structural elucidation of major selective androgen
More informationSupplementary Material. Efficient Synthesis of an Indinavir Precursor from Biomass Derived (-)- Levoglucosenone
1.171/CH17227_AC CSIRO 217 Australian Journal of Chemistry 217, 7(1), 1146-115 Supplementary Material Efficient Synthesis of an Indinavir Precursor from Biomass Derived (-)- Levoglucosenone Edward T. Ledingham,
More informationSupporting Information
Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 Supporting Information Potassium tert-butoxide Mediated Heck-Type Cyclization/Isomerization
More informationSupporting Information
Palladium-Catalyzed Cascade Oxidantion/sp 2 C-H Acylation of Azoarenes with Aryl Methanes Feng Xiong, a Cheng Qian, b Dongen Lin, b Wei Zeng b,* and Xiaoxia Lu a,* a Chengdu Institute of Biology,CAS, Chengdu
More informationChiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts. Jeremiah P. Malerich, Koji Hagihara, and Viresh H.
Chiral Squaramide Derivatives are Excellent ydrogen Bond Donor Catalysts Jeremiah P. Malerich, Koji agihara, and Viresh. Rawal* Department of Chemistry, University of Chicago, Chicago, Illinois 60637 E-mail:
More informationNHC-catalyzed cleavage of vicinal diketones and. triketones followed by insertion of enones and
Supporting Information for NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones Ken Takaki*, Makoto Hino, Akira Ohno, Kimihiro Komeyama, Hiroto Yoshida
More informationFacile Cu(II) mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Facile Cu(II) mediated conjugation of thioesters and thioacids to peptides
More informationSynthesis of cationic porphyrin modified amino. acids
Synthesis of cationic porphyrin modified amino acids Eric Biron and Normand Voyer* Département de chimie and CREFSIP, Faculté des sciences et de génie, Université Laval, Québec, Québec, Canada G1K 7P4
More informationSupporting Information
Supporting Information Synthesis and biological evaluation of Aryl-hospho-Indole (AI) as novel IV-1 non-nucleoside reverse transcriptase inhibitors. François-René Alexandre a *, Agnès Amador a, Stéphanie
More informationSupporting Online Material for
www.sciencemag.org/cgi/content/full/317/5837/496/dc1 Supporting nline Material for A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis Gregory L. amilton, Eun Joo Kang, Miriam
More informationThiol-Activated gem-dithiols: A New Class of Controllable. Hydrogen Sulfide (H 2 S) Donors
Thiol-Activated gem-dithiols: A New Class of Controllable Hydrogen Sulfide (H 2 S) Donors Yu Zhao, Jianming Kang, Chung-Min Park, Powell E. Bagdon, Bo Peng, and Ming Xian * Department of Chemistry, Washington
More informationby Donor-Acceptor Complex
Metal-Free C(sp 3 )-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex Yang Li 1+, Jing Zhang 1+, Defang Li 1,2, and Yiyun Chen 1,2 * Supplementary Information I. General Procedures...
More informationSupporting Information
Supporting Information for Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5- tetrafluorocyclohexane Mohammed Salah Ayoup 1,2, David B. Cordes 1,
More information