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Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

ABSTRACT: The direct asymmetric copper hydride (CuH)-catalyzed coupling of ?,?-unsaturated carboxylic acids to aryl alkenes to access chiral ?-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner.

SUBMITTER: Zhou Y

PROVIDER: S-EPMC5587210 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

Zhou Yujing Y Bandar Jeffrey S JS Buchwald Stephen L SL

Journal of the American Chemical Society 20170606 24

The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated ...[more]

PMID: 28565905

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