Issue 16, 2000

Asymmetric reduction of ethynyl ketones and ethynylketoesters by secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus

Abstract

Secondary alcohol dehydrogenase (SADH) from Thermoanaerobacter ethanolicus, an NADP-dependent, thermostable oxidoreductase, reduces ethynyl ketones and ethynylketoesters enantioselectively to the corresponding propargyl (propargyl = prop-2-ynyl) alcohols. Ethynyl ketones, in general, are reduced with moderate enantioselectivity (with the exception of 4-methylpent-1-yn-3-one, which gives the (S )-alcohol with >98% ee). Although ethynyl ketones bearing a small (up to n-propyl) alkyl substituent are reduced to (S )-alcohols, larger ethynyl ketones give (R)-alcohols. In contrast, ethynylketoesters are converted to (R)-ethynylhydroxyesters of excellent optical purity. Unexpectedly, isopropyl ethynylketoesters give higher chemical yields and higher enantioselectivities of ethynylhydroxyesters than methyl or ethyl ethynylketoesters. The optically pure ethynylhydroxyesters may serve as useful chiral building blocks for asymmetric synthesis.

Supplementary files

Article information

Article type
Paper
Submitted
17 Feb 2000
Accepted
23 May 2000
First published
10 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2821-2825

Asymmetric reduction of ethynyl ketones and ethynylketoesters by secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus

C. Heiss and R. S. Phillips, J. Chem. Soc., Perkin Trans. 1, 2000, 2821 DOI: 10.1039/B001329N

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