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Synlett

Volumn , Issue 14, 2008, Pages 2191-2195

Sulfur ylide mediated three-component aziridination and epoxidation reactions using vinyl sulfonium salts

(3) Kokotos, Christoforos G a McGarrigle, Eoghan M a Aggarwal, Varinder K a

a UNIVERSITY OF BRISTOL (United Kingdom)

Author keywords

Aziridinations; Epoxidations; Multicomponent reactions; Sulfur ylides; Vinyl sulfonium salts

Indexed keywords

ALDEHYDE; AZIRIDINE DERIVATIVE; DIPHENYLVINYL SULFONIUM TRIFLATE; EPOXIDE; IMINE; SULFONIUM DERIVATIVE; SULFUR DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; EPOXIDATION; SYNTHESIS;

EID: 51149113750 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078252 Document Type: Article

Times cited : (35)

References (35)

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22
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31
- 51149095274
- The products were characterized by NMR, IR, MS, and mp where appropriate, Satisfactory elemental analyses and/or HRMS were obtained for all compounds. Full details and spectra are available from the authors
- The products were characterized by NMR, IR, MS, and mp (where appropriate). Satisfactory elemental analyses and/or HRMS were obtained for all compounds. Full details and spectra are available from the authors.

32
- 51149124374
- N,4-Dimethyl-N, 1-(toluene-4-sulfonyl, 3-phenyl-2-aziridinyl]methyl}benzenesulfonamide (Table 2, Entry 2) cis-Isomer as a colourless oil; Rf, 0.40 (EtOAc-PE, 3:7, IR (film, 1598 (Ar, 1330 (SO2, 1160 (SO2) cm -1. 1H NMR (400 MHz, CDCl3, δ, 7.86 (2 H, d, J, 8.3 Hz, ArH, 7.50 (2 H, d, J, 8.3 Hz, ArH, 7.35 (2 H, d, J, 8.3 Hz, ArH, 7.27-7.16 (7 H, m, ArH, 3.93, 1 H, d, J, 7.0 Hz, NCHPh, 3.25-3.14 (2 H, m, NCHH and NCHCH2, 2.53 (1 H, dd, J, 14.3, 7.0 Hz, NCHH, 2.44 (6 H, s, 2 x CH 3, 2.38 (3 H, s, CH3, 13C NMR (100.5 MHz, CDCl3, δ, 145.0 (C, 143.5 (C, 136.2(C, 135.9(C, 132.0(C, 130.0(CH, 129.9 (CH, 129.7 (CH, 128.6 (CH, 128.3 (CH, 127.4 (CH, 127.3 (CH, 47.6 (CH2, 44.4 (CH, 44.1 (CH, 35.4 CH3, 21.7
- +].

33
- 51149083744
- Diethyl 2-Methyl-2, 1, 4-methylphenyl)sulfonyl]-3-phenyl-2- aziridinyl}methyl)malonate (Table 3, Entry 3) cis/trans-Isomers (3:1) as a colorless oil (89, Rf, 0.30 (EtOAc-PE, 2:8, IR (film, 1761 (OCO, 1162 (SO2) cm-1. 1H NMR (400 MHz, CDCl3, δ(cis, 7.85 (2 H, d, J, 8.3 Hz, ArH, 7.32-7.17 (7 H, m, ArH, 4.19-4.02 (4 H, m, 2 x OCH2, 3.87 (1 H, d, J, 7.2 Hz, NCHPh, 2.99-2.91 (1 H, m, NCHCH2, 2.43 (3 H, s, CH3, 1.87 (1 H, dd, J, 14.9, 5.8 Hz, CHH, 1.70 (1 H, dd, J, 14.9,6.4 Hz, CHH, 1.31 (3 H, s, CH3, 1.27-1.11 (6 H, m, 2 x CH3, 13C NMR (100.5 MHz, CDCl 3, δ, 171.5 (C, 171.4 (C, 144.7 (C, 144.6 (C, 132.4 (C, 129.8 (CH, 129.6 (CH, 128.5 (CH, 128.2 (CH, 127.6 (CH, 61.8 (CH 2, 61.6 (CH2, 52.4 (C, 45.1 (CH, 42.7 (CH, 31.1 CH
- 2Me].

34
- 51149106843
- 1-(4-Toluenesulfonyl)-2-phenyl-3, phenylsulfanyl)methyl]aziridine (Table 3, Entry 6) cis:trans-Isomers (1:5) as a colorless oil (33, Rf, 0.45 (EtOAc-PE, 3:7, IR (film, 1347 (SO 2, 1164 (SO2) cm-1. 1H NMR (400 MHz, CDCl3, δ(cis, 7.58 (2 H, d, J, 8.3 Hz, ArH, 7.35-7.08 (12 H, m, ArH, 4.03 (1 H, d, J, 7.0 Hz, NCHPh, 3.29-3.19 (2 H, m, NCHCHH, 2.62 (1 H, dd, J, 14.2, 7.0 Hz, CHH, 2.36 (3 H, s, CH3, 13C NMR (100.5 MHz, CDCl3, δ, 143.5 (C, 137.0 (C, 135.2 (C, 134.6 (C, 129.8 (CH, 129.7 (CH, 129.1 (CH, 128.8 (CH, 128.1 (CH, 127.7 (CH, 127.1 (CH, 126.6 (CH, 46.2 (CH, 45.1 (CH) 35.4 (CH2, 21.6 (CH3, 1H NMR (400 MHz, CDCl3, δ(trans, 7.81 (2 H, d, J, 8.3 Hz, ArH, 7.35-7.08 (12 H, m, ArH, 4.70 1 H, d, J
- +].

35
- 51149086651
- Diethyl 2-(Acetylamino)-2, 3-(4-rnethoxyphenyl)-1-(4-toluene- sulfonyl)-2-aziridinyl]methyl}malonate(Table4, Entry 8) cis-Isomer as a colorless oil (62, Rf, 0.40 (EtOAc-PE, 46, IR (film, 1762(OCO, 1160(SO2) cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.79 (2 H, d, J, 8.3 Hz, ArH, 7.29 (2 H, d, J, 8.3 Hz, ArH, 7.21 (1 H, br s, NH, 6.95 (2 H, d, J, 8.7 Hz, ArH, 6.75 (2 H, d, J, 8.7 Hz, ArH, 4.41-4.09 (4 H m, 2 x OCH 2, 3.74 (1 H, d, J, 7.2 Hz, NCHAr, 3.73 (3 H, s, OCH 3, 2.89 (1 H, ddd, J, 10.1, 7.2, 3.7 Hz, NCHCH 2, 2.53 (1 H, dd, J, 15.1, 3.7 Hz, CHH, 2.41 (3 H, s, CH3, 2 10 (1 H, dd, J, 15.1, 10.1 Hz, CHH, 2.07 (3 H, s, CH3, 1.33-1.15 (6 H, m, 2 x CH3, 13C NMR (100.5 MHz, CDCl3, δ, 169.7 (C, 167.4(C, 167.2C, 15
- + - TsNHAc].

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