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A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

ABSTRACT: We report a method for the highly enantioselective CuH-catalyzed allylation of ketones that employs terminal allenes as allylmetal surrogates. Ketones and allenes bearing diverse and sensitive functional groups are efficiently coupled with high stereoselectivity and exclusive branched regioselectivity. In stoichiometric experiments, each elementary step of the proposed hydrocupration-addition-metathesis mechanism can be followed by NMR spectroscopy.

SUBMITTER: Tsai EY

PROVIDER: S-EPMC5821421 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Tsai Erica Y EY Liu Richard Y RY Yang Yang Y Buchwald Stephen L SL

Journal of the American Chemical Society 20180202 6

We report a method for the highly enantioselective CuH-catalyzed allylation of ketones that employs terminal allenes as allylmetal surrogates. Ketones and allenes bearing diverse and sensitive functional groups are efficiently coupled with high stereoselectivity and exclusive branched regioselectivity. In stoichiometric experiments, each elementary step of the proposed hydrocupration-addition-metathesis mechanism can be followed by NMR spectroscopy. ...[more]

PMID: 29376366

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