Biocatalyst-Mediated Efficient Preparation of Highly Enantiomerically Enriched (R)-5-Hexanolide

Takeshi Sugai; Keiji Hamada; Tomohiro Akeboshi; Hajime Ikeda; Hiromichi Ohta

doi:10.1055/s-1997-972

Synlett 1997; 1997(8): 983-985
DOI: 10.1055/s-1997-972

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Biocatalyst-Mediated Efficient Preparation of Highly Enantiomerically Enriched (R)-5-Hexanolide

Takeshi Sugai, Keiji Hamada, Tomohiro Akeboshi, Hajime Ikeda, Hiromichi Ohta^*

^*Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Yokohama 223, Japan, Fax 81 45 563 5967; sugai@chem.keio.ac.jp

Abstract

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Biocatalyst-mediated efficient preparation of highly enantiomerically enriched (R)-5-hexanolide (1) is described. The enantioselective reduction of 5-oxohexanoic acid with Yamadazyma farinosa IFO 10896 and the subsequent lipase-catalyzed kinetic resolution gave (R)-1 in 62% yield with 99.7% e.e.

Yamadazyma farinosa - Pseudomonas lipase - enantioselective reduction - kinetic resolution - (R)-5-hexanolide

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