Supporting Information. were prepared from commercially available ethyl acetoacetate by alkylation with the
|
|
- Ashley Nash
- 5 years ago
- Views:
Transcription
1 ighly Stereoselective Reductions of α-alkyl-1,3-diketones and α- Alkyl-β-keto esters Catalyzed by Isolated NADP-dependent Ketoreductases Dimitris Kalaitzakis, a David J. Rozzell b, Spiros Kambourakis *b and Ioulia Smonou* a a Department of Chemistry, University of Crete, Iraklio 7149, Crete, Greece and b BioCatalytics Inc, 129 North ill Ave, Suite 13, Pasadena, CA 9116, USA Supporting Information Experimental Section General Considerations a-alkyl-1,3-diones 1-6 were prepared from commercially available 2,4-pentadione (acetylacetone) by alkylation with the proper alkyl halide. a-alkyl-β-keto esters 7, 8, were prepared from commercially available ethyl acetoacetate by alkylation with the proper alkyl halide. Racemic keto alcohols were prepared from pentan-2-one by aldol condensation with the corresponding aldehyde. Flash chromatography was carried out with 6 Å silica gel according to the procedure of Still (Still, W. C.; Kahn, M.; Mitra, A. J. rg. Chem. 1978, 14, ). The progress of the enzymatic reactions and the selectivities were determined by gas chromatography (P589II gas chromatograph equipped with an FID detector; column: 3m x.25mm x.25µm chiral capillary column, 2% permethylated cyclodextrin). MS were taken on a GC-MS (Simatzu GCMS-QP55 equipped with a S1
2 SPB-5 column and CI mass detector). 1 NMR and 13 C NMR spectra were recorded on a 3 Mz Bruker spectrometers in CDCl 3 solutions, by using Me 4 Si as internal standard. Chemical shifts are reported in ppm downfield from Me 4 Si. Yields refer to isolated and spectroscopically pure materials. Enzymatic Reductions Twenty different ketoreductases (KRED-11-12; BioCatalytics, Inc. Pasadena, CA USA) were screened to determine the best enzymes for the selective reduction of substrates methyl-2,4-pentanedione was used as the standard substrate. In addition to the ketoreductases, both NADP and glucose dehydrogenase (GLD) are products available from BioCatalytics. The screening was based in small-scale reactions (1 ml) where each substrate (25 mm) was mixed with NADP (2.5 mm, 2 mg), each ketoreductase (2 mg/ml), glucose (1 mm, 18 mg), glucose dehydrogenase (GLD, 2 mg/ml) for cofactor recycling, NaCl (1 mm, 6 mg) and sodium phosphate buffer (1 ml, 2 mm, p 6.9). The reactions were incubated at 37 ºC and reaction aliquots were taken every one hour and after extraction with ethyl acetate they were analyzed by GC chromatography. All the small-scale enzymatic reductions were accomplished according to the above screening reactions except for 3-methyl-2,4-pentanedione and 3-methyl-2,4-hexanedione which were reduced in p 6.5 and the reactions were completed in 24 hours. Larger-scale enzymatic reductions were prepared according to the following protocol. A phosphate-buffered solution (1 ml, p 6.9, 2 mm) containing 5 mm substrate, NaCl (2 mm), glucose (12 mm), NADP (.5 mm), glucose S2
3 dehydrogenase (5 mg) and the appropriate ketoreductase (5 mg) was stirred at 37 ºC for 24 hours, until GC analysis of crude extracts showed complete reaction. Periodically the p was readjusted to 6.9 with Na (2 M). Product was isolated by extracting the crude reaction mixture with EtAc (7 ml x 2). Sometimes centrifugation (6 rpm, 1 min) was required for the aqueous and the organic layers to separate as clear solutions. The combined organic layers were then extracted with saturated NaCl solution, dried over MgS 4 and evaporated to dryness. Pure, optically active alcohols were obtained in 9% to 91 % yield. The products were analyzed by NMR spectroscopy. Their optical purity was determined by chiral GC chromatography using 2% permethylated cyclodextrin column. According to this protocol diketone 1 (57 mg, 5 mm) was reduced with KRED12. Isolated yield 513 mg, 9%. 1 NMR: Ketoester 7 (72 mg, 5 mm) was reduced also with KRED12. Isolated yield 656 mg, 91%. Preparation of MPA-esters To a solution of the corresponding alcohol (.1 mmol) in dry C 2 Cl 2 were added 1.1 equiv. of DCC (.11 mmol) and 1.1 eqiv. f the corresponding (R) or (S) MPA (.11 mmol) and the reaction mixture was stirred at o C for 4-6 hr. After completion of the reaction the produced urea was filtered, the filtrate was evaporated and then chromatographed with 5/1 ex/etac and the produced corresponding MPA-ester was isolated. S3
4 Analytical and Spectral Data 1) GC analysis of racemic keto alcohol-1 with chiral capillary column, 2% permethylated cyclodextrin Sig. 1 in C:\PCEM\...\KALAITZ\123.D Time (min.) S4
5 2) 1 NMR (3 Mz, CDCl 3 ) of the racemic keto alcohol S5
6 3) GC analysis of the product, after enzymatic reduction of diketone-1 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\122.D Time (min.) S6
7 4) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-1 after enzymatic reduction with KRED S7
8 5) GC analysis of racemic keto alcohol-2 with chiral capillary column, 2% permethylated cyclodextrin Sig. 1 in C:\PCEM\...\KALAITZ\144.D Time (min.) S8
9 6) 1 NMR (3 Mz, CDCl 3 ) of the racemic keto alcohol S9
10 7) GC analysis of the product, after enzymatic reduction of diketone-2 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\145.D Time (min.) S1
11 8) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-2 after enzymatic reduction with KRED S11
12 9) GC analysis of the product, after enzymatic reduction of diketone-2 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1262.D Time (min.) S12
13 1) GC analysis of the product, after enzymatic reduction of diketone-2 with KRED118 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\626.D Time (min.) S13
14 11) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-2 after enzymatic reduction with KRED S14
15 12) GC analysis of racemic keto alcohol-3 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\452.D Time (min.) S15
16 13) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S16
17 14) GC analysis of the product, after enzymatic reduction of diketone-3 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\451.D Time (min.) S17
18 15) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-3 after enzymatic reduction with KRED S18
19 16) GC analysis of the product, after enzymatic reduction of diketone-3 with KRED114 (chiral capillary column, 2% permethylated cyclodextrin) 1.6e4 1.4e4 1.2e4 1.e Sig. 1 in C:\PCEM\...\KALAITZ\125.D Time (min.) S19
20 17) GC analysis of racemic keto alcohol-4 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1167.D Time (min.) S2
21 18) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S21
22 19) GC analysis of the product, after enzymatic reduction of diketone-4 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\416.D Time (min.) S22
23 2) GC analysis of the product, after enzymatic reduction of diketone-4 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1182.D Time (min.) S23
24 21) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-4 after enzymatic reduction with KRED S24
25 22) GC analysis of the product, after enzymatic reduction of diketone-4 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) 2.e4 1.8e4 1.6e4 1.4e4 1.2e4 1.e Sig. 1 in C:\PCEM\...\KALAITZ\124.D Time (min.) S25
26 23) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-4 after enzymatic reduction with KRED S26
27 24) GC analysis of racemic keto alcohol-5 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\223.D Time (min.) S27
28 25) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S28
29 26) GC analysis of the product, after enzymatic reduction of diketone-5 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\228.D Time (min.) S29
30 27) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-5 after enzymatic reduction with KRED S3
31 28) GC analysis of the product, after enzymatic reduction of diketone-5 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\735.D Time (min.) S31
32 29) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-5 after enzymatic reduction with KRED S32
33 3) GC analysis of the product, after enzymatic reduction of diketone-5 with KRED119 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1199.D Time (min.) S33
34 31) 1 NMR (5 Mz, CDCl 3 ) of the produced keto alcohol-5 after enzymatic reduction with KRED S34
35 32) GC analysis of racemic keto alcohol-6 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\161.D Time (min.) S35
36 33) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S36
37 34) GC analysis of the product, after enzymatic reduction of diketone-6 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\166.D Time (min.) S37
38 35) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-6 after enzymatic reduction with KRED S38
39 36) GC analysis of racemic hydroxy ester-7 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\316.D Time (min.) S39
40 37) 1 NMR (3 Mz, CDCl 3 ) of racemic hydroxy ester S4
41 38) GC analysis of the product, after enzymatic reduction of keto ester-7 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\322.D Time (min.) S41
42 39) 1 NMR (3 Mz, CDCl 3 ) of the produced hydroxy ester-7 after enzymatic reduction with KRED S42
43 4) GC analysis of the product, after enzymatic reduction of keto ester-7 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\338.D Time (min.) S43
44 41) 1 NMR (3 Mz, CDCl 3 ) of the produced hydroxy ester-7 after enzymatic reduction with KRED S44
45 42) GC analysis of racemic hydroxy ester-78(chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\326.D Time (min.) S45
46 43) 1 NMR (3 Mz, CDCl 3 ) of racemic hydroxy ester S46
47 44) GC analysis of the product, after enzymatic reduction of keto ester-8 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\33.D Time (min.) S47
48 45) 1 NMR (3 Mz, CDCl 3 ) of the produced hydroxy ester-8 after enzymatic reduction with KRED S48
49 46) GC analysis of the product, after enzymatic reduction of keto ester-8 with KRED116 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\58.D Time (min.) S49
50 47) 1 NMR (5 Mz, CDCl 3 ) of the produced hydroxy ester-8 after enzymatic reduction with KRED S5
51 Determination of absolute configuration of hydroxy compounds* MPA R 1 Me R 2 δ RS < δ RS > R 2 R 1 S Me Me R 1 Me R R 2 1 R R 2 2 R 1 or R2 R 1 Syn Me R 1 Me R R R R 1 R 1 or R2 R 1 Anti J vic (anti) > J vic (syn) *Seco, J. M.; Quinoa, E.; Riguera, R. Chem. Rev. 24, 14, Stiles, M.; Winkler, R. R.; Chang, Y.-L.; Traynor, L. J. Am. Chem. Soc.1964, 86, ouse,..; Crumrine, D. S.; Teranishi, A. Y.; lmstead,. D. J. Am. Chem. Soc.1973, 95, S51
52 48) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-1 produced after enzymatic reduction with KRED From 12 Me C C (R) S52
53 49) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-1 produced after enzymatic reduction with KRED From 12 Me C C (S) S53
54 5) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED12 5 From 12 Me C C (R) From 12 Me C C (R) S
55 51) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED From 12 Me C C (S) From 12 Me C C (S) S
56 52) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED From 118 Me C C (R) From 118 Me C C (R) S
57 53) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED From 118 Me C C (S) From 118 Me C C (S) S57
58 54) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-2 produced after enzymatic reduction with KRED12 (decoupling at 1.2ppm) From J vic (syn) = 4,9 z S58
59 55) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-2 produced after enzymatic reduction with KRED118 (decoupling at 1.24ppm) From J vic (anti) = 6.7 z S59
60 56) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S
61 57) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED12 25 From 12 Me C C (S) From 12 Me C C (S) S
62 58) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S
63 59) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED12 From 12 Me C C (S) From 12 Me C C (S) S
64 6) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-4 produced after enzymatic reduction with KRED12 (decoupling at 1.21ppm) From J vic (syn) = 4.7 z S64
65 61) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-4 produced after enzymatic reduction with KRED12 (decoupling at 1.25ppm) From J vic (anti) = 6.4 z S65
66 62) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED12 3 From 12 Me C C (R) From 12 Me C C (R) S
67 63) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED12 4 From 12 Me C C (S) From 12 Me C C (S) S
68 64) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED From 119 Me C C (R) From 119 Me C C (R) S
69 65) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED From 119 Me C C (S) From 119 Me C C (S) S
70 66) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-5 produced after enzymatic reduction with KRED12 (decoupling at 1.2ppm) From J vic (syn) = 4.5 z S7
71 67) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-5 produced after enzymatic reduction with KRED119 (decoupling at 1.24ppm) From J vic (anti) = 6.3 z S71
72 68) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-6 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S
73 69) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-6 produced after enzymatic reduction with KRED From 12 Me C C (S) From 12 Me C C (S) S
74 7) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S
75 71) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED12 4 From 12 Me C C (S) From 12 Me C C (S) S
76 72) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED From 17 Me C C (R) From 17 Me C C (R) S
77 73) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED17 1 From 17 Me C C (S) From 17 Me C C (S) S
78 74) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S78 1..
79 75) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED From 12 Me C C (S) From 12 Me C C (S) S
80 76) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED From 116 Me C C (R) From 116 Me C C (R) S
81 77) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED116 2 From 116 Me C C (S) From 116 Me C C (S) S81 1..
82 78) 1 NMR (5 Mz, CDCl 3 ) of hydroxy ester-8 produced after enzymatic reduction with KRED12 (decoupling at 1.21ppm) From J vic (syn) = 5 z S82
83 79) 1 NMR (5 Mz, CDCl 3 ) of hydroxy ester-8 produced after enzymatic reduction with KRED116 (decoupling at 1.24ppm) From J vic (anti) = 6 z S83
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 informationDeveloping a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles
Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles Elisa Liardo, a Nicolás Ríos-Lombardía, b Francisco Morís, b Javier González-Sabín,*,b and
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 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 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 informationAcyl Radical Reactions in Fullerene Chemistry: Direct Acylation of. [60]Fullerene through an Efficient Decatungstate-Photomediated Approach.
Supporting information Acyl Radical Reactions in Fullerene Chemistry: Direct Acylation of [60]Fullerene through an Efficient Decatungstate-Photomediated Approach. Manolis D. Tzirakis and Michael rfanopoulos
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 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 informationTwo chiral centres (diastereoisomers)
1 Two chiral centres (diastereoisomers) Mirror N S N Two enantiomers differ by absolute configuration N N 2 N 2 N A molecule with 1 stereogenic centre exists as 2 stereoisomers or enantiomers Enantiomers
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 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 informationSupplemental materials for:
Tambar and Stoltz, Supporting Information 1 Supplemental materials for: The Direct Acyl-Alkylation of Arynes Uttam K. Tambar and Brian M. Stoltz* The Arnold and Mabel Beckman Laboratories of Chemical Synthesis,
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 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 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 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 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 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 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 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 informationThe First Au-Nanoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine
Supporting information of The First Au-anoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine Mazaahir Kidwai a *, Vikas Bansal a,
More informationCopyright Wiley-VCH Verlag GmbH, D Weinheim, Angew. Chem
Copyright Wiley-VCH Verlag GmbH, D-69451 Weinheim, 2000. Angew. Chem. 2000. Supporting Information for Salen as Chiral Activator : Anti vs Syn Switchable Diastereoselection in the Enantioselective Addition
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 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 informationA biocatalytic hydrogenation of carboxylic acids
Electronic Supplementary Information (ESI) for: A biocatalytic hydrogenation of carboxylic acids Yan Ni, Peter-Leon Hagedoorn,* Jian-He Xu, Isabel Arends, Frank Hollmann* 1. General Chemicals All the carboxylic
More informationSupporting Information
Supporting Information Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions. Laurence Burroughs, Paul A. Clarke,* Henrietta Forintos, James
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 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 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 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 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. 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 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 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 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 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 informationSalenCo(OAc)/chiral ionic liquid catalyzed the asymmetric cycloaddition of CO 2 to epoxides
Supporting information SalenCo(OAc)/chiral ionic liquid catalyzed the asymmetric cycloaddition of CO 2 to epoxides Suling Zhang, Yongzhong Huang, Huanwang Jing*, Weixuan Yao, Peng Yan State Key Laboratory
More informationSupporting Information
Notes Bull. Korean Chem. Soc. 2013, Vol. 34, No. 1 1 http://dx.doi.org/10.5012/bkcs.2013.34.1.xxx Supporting Information Chemical Constituents of Ficus drupacea Leaves and their α-glucosidase Inhibitory
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 informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Phosphine-Mediated Disulfide Metathesis in Aqueous Media Rémi Caraballo, Morakot Sakulsombat, and Olof Ramström* KTH - Royal Institute of Technology, Department of Chemistry Teknikringen
More informationBase-promoted acetal formation employing aryl salicylates
Base-promoted acetal formation employing aryl salicylates Pinmanee Boontheung, Patrick Perlmutter*, and Evaloni Puniani School of Chemistry, Monash University, PO Box 23, Victoria 3800 Australia E-mail:
More informationNational Defense Academy, Hashirimizu, Yokosuka, , Japan
Suppoing Information for Reaction of Arynes with Amino Acid Esters Kentaro kuma, a * ahoko Matsunaga, a oriyoshi agahora, a Kosei Shioji, a and Yoshinobu Yokomori b a Depament of Chemistry, Faculty of
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 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 informationSupporting Information. Radical fluorination powered expedient synthesis of 3 fluorobicyclo[1.1.1]pentan 1 amine
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Radical fluorination powered expedient synthesis
More informationNaoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
Supplementary material Facile transformation of the five-membered exocyclic E-ring in 13 2 -demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi,
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 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 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 informationZn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH 4 Cl Solution
Molecules 2001, 6, 964-968 molecules ISSN 1420-3049 http://www.mdpi.org Zn Mediated egioselective Barbier eaction of Propargylic Bromides in TF/aq. N 4 Cl Solution Artur Jõgi and Uno Mäeorg* Institute
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 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 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 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 informationPh 2 SO-Tf 2 O: a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides
Ph 2 SO-Tf 2 O: a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides Jeroen D. C. Codée, Remy E. J. N. Litjens, René den Heeten, Herman S. Overkleeft, Jacques H. van Boom, Gijsbert
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 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 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 informationA Hierarchy of Aryloxide Deprotection by Boron Tribromide. Supporting Information
A Hierarchy of Aryloxide Deprotection by Boron Tribromide Sreenivas Punna, Stéphane Meunier and M. G. Finn* Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute,
More informationSupporting Information. Palladium-catalyzed reductive cleavage of tosylated arene using isopropanol as the mild reducing agent
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2014 Supporting Information Supporting Information Palladium-catalyzed reductive cleavage
More informationOrganocatalytic Asymmetric Transferhydrogenation of β- Nitroacrylates: Accessing β²-amino Acids
rganocatalytic Asymmetric Transferhydrogenation of β- Nitroacrylates: Accessing β²-amino Acids Nolwenn J. A. Martin, Xu Cheng and Benjamin List* Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim
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 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 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 informationEfficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide
More informationEnzymatic resolution and evaluation of enantiomers of. cis-5 -hydroxythalidomide
Electronic Supplementary Information Enzymatic resolution and evaluation of enantiomers of cis-5 -hydroxythalidomide Takeshi Yamamoto, a orio Shibata, a * Masayuki Takashima, a Shuichi akamura, a Takeshi
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 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 informationCDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines
Supporting information: CDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines Sanjeev K. Verma*, Ramarao Ghorpade, Ajay Pratap and M. P.
More informationEur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2009 ISSN X SUPPORTING INFORMATION
Eur. J. rg. Chem. 2009 WILEY-VC Verlag Gmb & Co. KGaA, 69451 Weinheim, 2009 ISS 1434 193X SUPPRTIG IFRMATI Title: ew GM1 Ganglioside Derivatives for Selective Single and Double Labelling of the atural
More informationUse of degradable cationic surfactants with cleavable linkages for enhancing the. chemiluminescence of acridinium ester labels. Supplementary Material
Use of degradable cationic surfactants with cleavable linkages for enhancing the chemiluminescence of acridinium ester labels Supplementary Material Anand atrajan*and David Wen Siemens Healthcare Diagnostics
More informationmolecules ISSN
Molecules 2006, 11, 357-364 Full Paper molecules ISSN 1420-3049 http://www.mdpi.org Synthesis of Novel Sterically Demanding Carbo- and Heterocyclic β-ketoesters Marko D. Mihovilovic,* Thomas C. M. Fischer
More informationSupporting information
Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 214 Striking difference between alkane and olefin metathesis by the well-defined
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 FOR. Regioselective Ring-opening and Isomerization Reactions of 3,4-Epoxyesters Catalyzed by Boron Trifluoride
S1 SUPPORTING INFORMATION FOR Regioselective Ring-opening and Isomerization Reactions of 3,4-Epoxyesters Catalyzed by Boron Trifluoride Javier Izquierdo, Santiago Rodríguez and Florenci V. González* Departament
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 informationEasily removable olefin metathesis catalysts
Easily removable olefin metathesis catalysts Krzysztof Skowerski,*a Celina Wierzbicka,a Grzegorz Szczepaniak,b Łukasz Gułajski, a Michał Bieniek, a and Karol Grela*b a Apeiron Synthesis Sp. z o.o., Klecińska
More informationSelf-organization of dipyridylcalix[4]pyrrole into a supramolecular cage for dicarboxylates
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information Self-organization of dipyridylcalix[4]pyrrole into a supramolecular
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 informationPreparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas
SUPPORTING INFORMATION Preparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas Vommina V. Suresh Babu*, Basanagoud S. Patil, and Rao Venkataramanarao
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 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 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 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
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 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. 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 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 informationSupplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Experimental Details Unless otherwise noted, all chemicals were purchased from Sigma-Aldrich Chemical Company and were used as received. 2-DOS and neamine were kindly provided by Dr. F. Huang. Paromamine
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 informationA pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state
A pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state Mingguang Pan, Min Xue* Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China Fax:
More informationSupporting Information
Supporting Information A single design strategy for dual sensitive ph probe with a suitable range to map ph in living cells Kang-Kang Yu, Ji-Ting Hou, Kun Li, * Qian Yao, Jin Yang, Ming-Yu Wu, Yong-Mei
More informationTHE JOURNAL OF ANTIBIOTICS. Polyketomycin, a New Antibiotic from Streptomyces sp. MK277-AF1. II. Structure Determination
THE JOURNAL OF ANTIBIOTICS Polyketomycin, a New Antibiotic from Streptomyces sp. MK277-AF1 II. Structure Determination ISAO MOMOSE, WEI CHEN, HIKARU NAKAMURA, HIROSHI NAGANAWA, HIRONOBU IINUMA and TOMIO
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. 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 informationSupplementary Information
Supplementary Information Ruthenium(IV) porphyrin catalyzed phosphoramidation of aldehyde with phosphoryl azide as nitrene source Wenbo Xiao, Cong-Ying Zhou and Chi-Ming Che* Department of Chemistry, State
More informationConversion of a-amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid
SYNTHETIC COMMUNICATIONS w Vol. 34, No. 19, pp. 3449 3453, 2004 Conversion of a-amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid Gene A. Hiegel,* Justin C. Lewis, and
More informationSupporting Information File 1. for. Synthesis of functionalised β-keto amides by. aminoacylation/domino fragmentation of β-enamino amides
Supporting Information File 1 for Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides Pavel Yanev and Plamen Angelov* Address: Department of Organic Chemistry,
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 informationDirect Regioselective Esterification at O-2 of β- Cyclodextrin and Hydrolysis by Neighboring-group Participation
ISSN: 0973-4945; CDEN ECJHA E- Chemistry http://www.ejchem.net 2012, 9(3), 1562-1568 Direct Regioselective Esterification at -2 of β- Cyclodextrin and Hydrolysis by Neighboring-group Participation ZHI-ZHNG
More information