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CuH-Catalyzed Asymmetric Reduction of ?,?-Unsaturated Carboxylic Acids to ?-Chiral Aldehydes.

ABSTRACT: The copper hydride (CuH)-catalyzed enantioselective reduction of ?,?-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of ?-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.

SUBMITTER: Zhou Y

PROVIDER: S-EPMC5800953 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Zhou Yujing Y Bandar Jeffrey S JS Liu Richard Y RY Buchwald Stephen L SL

Journal of the American Chemical Society 20180104 2

The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of 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 based on preliminary mechanistic studies and density functional theory calculations. ...[more]

PMID: 29283578

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