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Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C=C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones.

Research paper by Ji J Liu, Jinchuan J Wu, Zhi Z Li

Indexed on: 16 Jul '14Published on: 16 Jul '14Published in: Chemical Communications



Abstract

Enoyl-ACP reductase (FabI) was identified as a non-OYE 'ene'-reductase for asymmetric reduction of the C=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.