Sequential kinetic resolution of (±)-2,3-butanediol in organic solvent using lipase from Pseudomonas cepacia.

Gaétan Caron, Romas J. Kazlauskas

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

Lipase from Pseudomonas cepocia (PCL, Amano FS) catalyzed the enantioselective diacetylation of (±)-23-butanediol in vinyl acetate. Both acetylation steps favored the (R)-enantiomer (E1 = 12, E2 = 34), thus the reaction is a sequential kinetic resolution. The enantioselectivities of the two steps reinforced one another because both steps proceeded at comparable rates (S = 3) yielding an overall enantioselectivity of approximately 200. A synthetic-scale resolution starting from 2.7 g of (±)-2,3-butanediol yielded the diacetate ester of (R)-(-)-butanediol with 96% ee (1.6 g, 30% yield) and (S)-(+)-butanediol with 99% ee (0.63 g, 23% yield). This preparation is carried out entirely in organic solvent, thereby avoiding the difficult and low yield extraction of 2,3-butanediol from aqueous aolution.

Original languageEnglish (US)
Pages (from-to)1995-2000
Number of pages6
JournalTetrahedron: Asymmetry
Volume4
Issue number9
DOIs
StatePublished - 1993

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