Improvement of enantioselectivity in kinetic resolution of a primary alcohol through lipase-catalyzed transesterification by using a chiral acyl donor

Keiji Hirose*, Hiroyuki Naka, Masashi Yano, Sozaburo Ohashi, Koichiro Naemura, Tobe Yoshito

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

The enantioselectivity of the kinetic resolution of a primary alcohol which has a chiral center at the β-position of the hydroxyl group was substantially improved by employing a racemic mixture of a chiral acyl donor for enantioselective transesterification catalyzed by a lipase. The combination of the lipase, solvent, and acyl donor was also effective for the enantioselectivity. In addition, the important effect of the chirality of an acyl donor on kinetic resolution was investigated by using enantiomerically pure acyl donors. Here we demonstrate the effective kinetic resolution (E=98) of a primary alcohol, 2-phenyl-1-propanol, by using a racemic mixture of a chiral acyl donor, vinyl 3-phenylbutanoate. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)1199-1210
Number of pages12
JournalTetrahedron Asymmetry
Volume11
Issue number5
DOIs
StatePublished - 24 Mar 1999

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