| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347167 | Tetrahedron: Asymmetry | 2009 | 8 Pages |
The work describes a new enzyme-mediated approach to optically active epoxide (2R,3S)-6, which is an important key intermediate in the preparation of single enantiomers of chiral azole antifungals. The conversion of (2R,3S)-6 into (−)-genaconazole is reported as an example of its synthetic relevance.
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(2R,3R)-2-(2,4-Difluorophenyl)-2-hydroxybutane-1,3-diyl diacetateC14H16F2O5Ee = 99%[α]D24=-22.6 (c 0.93, CHCl3)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (2R,3R)
(2R,3R)-2-(2,4-Difluorophenyl)butane 1,2,3-triolC10H12F2O3Ee = 99%[α]D24=+5.7 (c 0.88, acetone)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (2R,3R)
1-(((2R,3S)-2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazoleC12H11F2N3OEe = 99%[α]D24=-12.2 (c 0.96, CHCl3)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (2R,3S)
(2R,3R)-2-(2,4-Difluorophenyl)-3-(methylthio)-1-(1H-1,2,4-triazol-1-yl)butan-2-olC13H15F2N3OSEe = 99%[α]D24=-126.7 (c 0.5, CHCl3)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (2R,3R)
(2R,3R)-2-(2,4-Difluorophenyl)-3-(methylsulfonyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-olC13H15F2N3O3SEe = 99%[α]D24=-36.9 (c 0.98, MeOH)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (2R,3R)
(S)-2-Hydroxy-2-phenylbut-3-enyl acetateC12H14O3Op = 15%[α]D24=-6.0 (c 2.5, EtOH)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (S)
(S)-2-Phenylbut-3-ene-1,2-diolC10H12O2Op = 15%[α]D24=-7.1 (c 1.1, EtOH)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (S)
(R)-1-((S)-4-(2,4-Difluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetateC15H18F2O4Ee = 99%[α]D24=+54.3 (c 0.6, CHCl3)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (R,S)
(R)-1-((S)-2,2-Dimethyl-4-phenyl-1,3-dioxolan-4-yl)ethyl acetateC15H20O4Ee = 99%[α]D24=+34.4 (c 1.20, CHCl3)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (R,S)
(R)-1-((S)-4-(4-Fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetateC15H19FO4Ee = 99%[α]D24=+29.7 (c 1.16, CHCl3)Source of chirality: lipase-mediated transesterificationAbsolute configuration: (R,S)
