S. Ghorpade, K. B. Bastawade, D. Gokhale
Oct 29, 1999
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Influential Citations
23
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Enzymatic kinetic resolution studies of (±)-4-hydroxycyclopent-2-en-1-one 2 were taken up in organic solvents by transesterification with vinyl acetate and alcoholysis of its acetate 3 as an alternative to the desymmetrization of meso-cyclopentenediol to provide faster and economic access to enantiomerically pure 4-(R)-tert-butyldimethylsilyloxycyclopent-2-en-1-one 1. Parameters were screened using Lipozyme IM® as catalyst. Although enantioselectivity observed was moderate (E=24, by alcoholysis of 3 with 2-butanol), trends in the effect of solvent, water content and alcohol structure showed useful directions for screening of other enzymes for optimization of the method to useful levels of efficiency.