| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350635 | Tetrahedron: Asymmetry | 2007 | 7 Pages |
A simple method for the preparation of optically active 2-(arylsulfanylmethyl)thiiranes and 2-(aryloxymethyl)thiiranes from the corresponding 3-thiocyanatopropan-2-ols and their acetates was developed. The starting enantiomerically enriched β-thiocyanatoalcohols and the acetates were obtained by a lipase-catalyzed hydrolysis of the appropriate racemic acetates.
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(S)-(+)-1-Phenylsuphanyl-3-thiocyanatopropan-2-olC10H11NS2OEe = 96%[α]D25 = +7.2 (c 9.76, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(S)-(+)-1-(4-Chlorophenylsuphanyl)-3-thiocyanatopropan-2-olC10H10NS2ClOEe = 98%[α]D23 = +9.4 (c 4.67, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(S)-(+)-1-(4-Bromophenylsuphanyl)-3-thiocyanatopropan-2-olC10H10NS2BrOEe = 85%[α]D23.5 = +6.4 (c 1.71, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(S)-(+)-1-Thiocyanato-3-(p-tolylsulfanyl)propan-2-olC11H13NS2OEe = 80%[α]D27 = +5.7 (c 0.87, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(R)-(−)-1-Phenylsulfanyl-3-thiocyanatopropan-2-yl acetateC12H13NS2O2Ee = 90%[α]D28 = −8.4 (c 5, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-1-(4-Chlorophenylsulfanyl)-3-thiocyanatopropan-2-yl acetateC12H12NClS2O2Ee = 58%[α]D23 = −0.65 (c 9.21, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-1-(4-Bromophenylsulfanyl)-3-thiocyanatopropan-2-yl acetateC12H12NBrS2O2Ee = 61%[α]D23.5 = 0 (c 4.3, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-3-Thiocyanato-1-(p-tolylsulfanyl)propan-2-yl acetateC13H15NS2O2Ee = ND[α]D23 = −1.9 (c 5.14, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(S)-(+)-2-(Phenylsulfanylmethyl)thiiraneC9H10S2Ee = 86%[α]D24 = +71.4 (c 6.78, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
(S)-(+)-2-(4-Chlorophenylsulfanylmethyl)thiiraneC9H9S2ClEe = 53%[α]D24 = +35.2 (c 5.47, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
(S)-(+)-2-(4-Bromophenylsulfanylmethyl)thiiraneC9H9S2BrEe = 59%[α]D24 = +33.0 (c 4.36, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
(S)-(+)-2-(p-Tolylsulfanylmethyl)thiiraneC10H12S2Ee = 32%[α]D24 = +24.2 (c 4.54, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
(S)-(−)-2-(Phenoxymethyl)thiiraneC9H10SOEe = 97%[α]D25 = −13.6 (c 2.8, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
(S)-(−)-2-(4-Chlorophenoxymethyl)thiiraneC9H9ClSOEe = 90%[α]D25 = −12.5 (c 4.64, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
(S)-(−)-2-(p-Tolyloxymethyl)thiiraneC10H12SOEe = 86%[α]D25 = −10.7 (c 4.48, CHCl3)Source of chirality: chemo-enzymatic synthesisAbsolute configuration: (S)
