Issue 68, 2014

Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C[double bond, length as m-dash]C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones

Abstract

Enoyl-ACP reductase (FabI) was identified as a non-OYE ‘ene’-reductase for asymmetric reduction of the C[double bond, length as m-dash]C double bond of α, β-unsaturated ketones. Reduction of several 2-alkylidenecyclopentanones with A-FabI and E-FabI gave (R)-2-alkylcyclopentanones in 95–90% and 70–81% ee, respectively. The product ee was improved to 99–98% in high yield by subsequent one-pot biooxidation.

Graphical abstract: Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C [[double bond, length as m-dash]] C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones

Supplementary files

Article information

Article type
Communication
Submitted
30 May 2014
Accepted
04 Jul 2014
First published
04 Jul 2014
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2014,50, 9729-9732

Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C[double bond, length as m-dash]C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones

J. Liu, J. Wu and Z. Li, Chem. Commun., 2014, 50, 9729 DOI: 10.1039/C4CC04150J

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