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CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes

Yujing Zhou, Jeffrey S. Bandar, Richard Y. Liu and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

Y. Zhou, J. S. Bandar, R. Y. Liu, S. L. Buchwald, J. Am. Chem. Soc., 2018, 140, 606-609.

DOI: 10.1021/jacs.7b12260 (free Supporting Information)


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Abstract

A copper hydride-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids provides various saturated β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed.

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proposed mechanism



Key Words

1,4-Reduction, Reduction of Carboxylic Acids, Copper Hydride, Dimethoxymethylsilane


ID: J48-Y2018