Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters José A. Carmona, a Gonzalo de Gonzalo, b Inmaculada Serrano, b, Ana M. Crespo-Peña, a Michal Šimek, a David Monge,*,b Rosario Fernández*,b and José M. Lassaletta*,a Instituto de Investigaciones Químicas (CSIC-US), C/ Américo Vespucio 49, Sevilla (Spain), and Departamento de Química Orgánica, Universidad de Sevilla, C/ Prof. García González, 1, Sevilla (Spain) dmonge@us.es; ffernan@us.es; jmlassa@iiq.csic.es CONTENTS 1. NMR Spectra GC Chromatograms HPLC Chromatograms
2 1. NMR Spectra: 1 H NMR (CDCl 3, 500 MHz) of VIII: 13 C NMR (CDCl 3, 125 MHz) of VIII: 2
3 1 H NMR (CD 3 OD, 500 MHz) of 9a: 13 C NMR (CD 3 OD, 125 MHz) of 9a: 3
4 1 H NMR (CD 3 OD, 500 MHz) of 10a: 13 C NMR (CD 3 OD, 125 MHz) of 10a: 4
5 1 H NMR (CDCl 3, 400 MHz) of IX: 13 C NMR (CDCl 3, 100 MHz) of IX: 5
6 1 H NMR (CDCl 3, 500 MHz) of X: 13 C NMR (CDCl 3, 125 MHz) of X: 6
7 1 H NMR (CDCl 3, 500 MHz) of XI: 13 C NMR (CDCl 3, 125 MHz) of XI: 7
8 1 H NMR (CDCl 3, 400 MHz) of XII: OBz BzO O BzO HN OBz S HN CF 3 XII CF 3 13 C NMR (CDCl 3, 100 MHz) of XII: 8
9 1 H NMR (CDCl 3, 300 MHz) of XIII: OPiv PivO O PivO HN OPiv S HN CF 3 XIII CF 3 13 C NMR (CDCl 3, 75 MHz) of XIII: 9
10 1 H NMR (CDCl 3, 400 MHz) of [(S)-3a]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-3a]: 10
11 1 H NMR (CDCl 3, 400 MHz) of [(S)-3b]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-3b]: 11
12 1 H NMR (CDCl 3, 300 MHz) of [(S)-3c]: 13 C NMR (CDCl 3, 125 MHz) of [(S)-3c]: 12
13 1 H NMR (CDCl 3, 400 MHz) of [(S)-3d]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-3d]: 13
14 1 H NMR (CDCl 3, 300 MHz) of [(S)-3e]: 13 C NMR (CDCl 3, 75 MHz) of [(S)-3e]: 14
15 1 H NMR (CDCl 3, 400 MHz) of [(S)-3f]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-3f]: 15
16 1 H NMR (CDCl 3, 400 MHz) of [(S)-3g]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-3g]: 16
17 1 H NMR (CDCl 3, 400 MHz) of [(S)-4a]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-4a]: 17
18 1 H NMR (CDCl 3, 500 MHz) of [(S)-4b]: 13 C NMR (CDCl 3, 125 MHz) of [(S)-4b]: 18
19 1 H NMR (CDCl 3, 300 MHz) of [(S)-4c]: 13 C NMR (CDCl 3, 125 MHz) of [(S)-4c]: 19
20 1 H NMR (CDCl 3, 400 MHz) of [(S)-4d]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-4d]: 20
21 1 H NMR (CDCl 3, 300 MHz) of [(S)-4e]: 13 C NMR (CDCl 3, 75 MHz) of [(S)-4e]: 21
22 1 H NMR (CDCl 3, 400 MHz) of [(S)-4f]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-4f]: 22
23 1 H NMR (CDCl 3, 400 MHz) of [(R)-4h]: 13 C NMR (CDCl 3, 100 MHz) of [(R)-4h]: 23
24 1 H NMR (CDCl 3, 400 MHz) of [(R)-4i]: 13 C NMR (CDCl 3, 100 MHz) of [(R)-4i]: 24
25 1 H NMR (CDCl 3, 400 MHz) of [(R)-4j]: 13 C NMR (CDCl 3, 100 MHz) of [(R)-4j]: 25
26 1 H NMR (CDCl 3, 300 MHz) of [(R)-4k]: 13 C NMR (CDCl 3, 75 MHz) of [(R)-4k]: 26
27 1 H NMR (CDCl 3, 300 MHz) of [(R)-4l]: 13 C NMR (CDCl 3, 75 MHz) of [(R)-4l]: 27
28 1 H NMR (CDCl 3, 300 MHz) of [(S)-5a]: 13 C NMR (CDCl 3, 75 MHz) of [(S)-5a]: 28
29 1 H NMR (CDCl 3, 300 MHz) of [(S)-5c]: 13 C NMR (CDCl 3, 75 MHz) of [(S)-5c]: 29
30 1 H NMR (CDCl 3, 300 MHz) of [(S)-5d]: 13 C NMR (CDCl 3, 75 MHz) of [(S)-5d]: 30
31 1 H NMR (CDCl 3, 300 MHz) of [(S)-5e]: 13 C NMR (CDCl 3, 75 MHz) of [(S)-5e]: 31
32 1 H NMR (CDCl 3, 400 MHz) of [(S)-5f]: 13 C NMR (CDCl 3, 100 MHz) of [(S)-5f]: 32
33 1 H NMR (CDCl 3, 300 MHz) of [(R)-5h]: 13 C NMR (CDCl 3, 75 MHz) of [(R)-5h]: 33
34 1 H NMR (CDCl 3, 300 MHz) of [(R)-5i]: 13 C NMR (CDCl 3, 75 MHz) of [(R)-5i]: 34
35 1 H NMR (CDCl 3, 400 MHz) of [(R)-5j]: 13 C NMR (CDCl 3, 100 MHz) of [(R)-5j]: 35
36 1 H NMR (CDCl 3, 300 MHz) of [(R)-5k]: 13 C NMR (CDCl 3, 75 MHz) of [(R)-5k]: 36
37 1 H NMR (CDCl 3, 300 MHz) of [(R)-5l]: 13 C NMR (CDCl 3, 75 MHz) of [(R)-5l]: 37
38 2. GC Chromatograms GC conditions for 3a: Chrompack CP7500, cyclodextrin-β, 225m x 0.25 mm x 0.25 μm, He as mobile phase 38
39 GC conditions for (S)-3b: Chrompack CP7500, cyclodextrin-β, 225m x 0.25 mm x 0.25 µm, He as mobile phase 39
40 3. HPLC Chromatograms HPLC conditions for (S)-3c: Chiralpak AD-H column [hexane/i-proh (98:2) 1 ml/min] HPLC conditions for (S)-3e: Chiralpak OJ-H column [hexane/ i PrOH (98:2) 1 ml/min] 40
![HPLC conditions for (S)-4a: Chiralpak AD-H column [hexane/i-proh (98:2) 1 ml/min]](/docs-images/92/108477431/images/41-4.jpg "HPLC conditions for (S)-4b: Chiralpak OJ column [hexane/i-proh (98:2) 1 ml/min]")
41 HPLC conditions for (S)-4a: Chiralpak AD-H column [hexane/i-proh (98:2) 1 ml/min] HPLC conditions for (S)-4b: Chiralpak OJ column [hexane/i-proh (98:2) 1 ml/min] 41
![ml/min] HPLC conditions for (S)-4d:](/docs-images/92/108477431/images/42-5.jpg "Chiralpak AD-H column [hexane/i-proh")
42 HPLC conditions for (S)-4c: Chiralpak AD-H column [hexane/i-proh (98:2) 1 ml/min] HPLC conditions for (S)-4d: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min] 42
![HPLC conditions for (S)-4e: Chiralpak OJ-H column [hexane/ i PrOH (98:2) 1 ml/min]](/docs-images/92/108477431/images/43-0.jpg "HPLC conditions for (S)-4f: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min]")
43 HPLC conditions for (S)-4e: Chiralpak OJ-H column [hexane/ i PrOH (98:2) 1 ml/min] HPLC conditions for (S)-4f: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min] 43
![HPLC conditions for (S)-4g: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min]](/docs-images/92/108477431/images/44-4.jpg "HPLC conditions for (R)-4h: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min]")
44 HPLC conditions for (S)-4g: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min] HPLC conditions for (R)-4h: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min] 44
![HPLC conditions for (R)-4i: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min]](/docs-images/92/108477431/images/45-1.jpg "HPLC conditions for (R)-4j: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min]")
45 HPLC conditions for (R)-4i: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min] HPLC conditions for (R)-4j: Chiralpak AD-H column [hexane/i-proh (80:20) 1 ml/min] 45
46 HPLC conditions for (R)-4k: Chiralpak AD-H column [hexane/ i PrOH (98:2) 1 ml/min] HPLC conditions for (R)-4l: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] 46
47 HPLC conditions for (S)-5a: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] HPLC conditions for (S)-5c: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] 47
48 HPLC conditions for (S)-5d: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] HPLC conditions for (S)-5e: Chiralpak OJ-H column [hexane/ i PrOH (90:10) 1 ml/min] 48
49 HPLC conditions for (S)-5f: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] HPLC conditions for (R)-5h: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] 49
![HPLC conditions for (R)-5i: Chiralpak IB column [hexane/ i PrOH (90:10) 1 ml/min]](/docs-images/92/108477431/images/50-4.jpg "HPLC conditions for (R)-5j: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min]")
50 HPLC conditions for (R)-5i: Chiralpak IB column [hexane/ i PrOH (90:10) 1 ml/min] HPLC conditions for (R)-5j: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] 50
51 HPLC conditions for (R)-5k: Chiralpak IA column [hexane/ i PrOH (80:20) 1 ml/min] HPLC conditions for (R)-5l: Chiralpak AD-H column [hexane/ i PrOH (80:20) 1 ml/min] 51
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