Article ID Journal Published Year Pages File Type
1346108 Tetrahedron: Asymmetry 2005 6 Pages PDF
Abstract

Hydroxyacetals 2 and 3 were resolved by acylation with vinyl acetate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding acetates, was also highly stereoselective and provided the opposite enantiomers.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

(2S)-1,1-Dimethoxybut-3-en-2-olC6H12O3Ee = 93% (chiral GC)[α]D22=-32.7 (c 1.28, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: 2S

(1R)-1-(Dimethoxymethyl)prop-2-enyl acetateC8H14O4Ee = 95% (chiral GC)[α]D22=+27.5 (c 1.23, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: 1R

(2R)-1,1-Dimethoxypent-4-en-2-olC7H14O3Ee = 98% (chiral GC)[α]D22=+8.8 (c 1.17, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: 2R

(1S)-1-(Dimethoxymethyl)but-3-enyl acetateC9H16O4Ee = 96% (chiral GC)[α]D22=+14.4 (c 0.98, CHCl3)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (1S)

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
Authors
, , ,