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Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

ABSTRACT: A reaction between epoxides and benzylboronic acid pinacol esters is described. CuI was found to be an effective catalyst of this transformation upon activation of the benzylboronic ester with an alkyllithium reagent. The reaction was very efficient and a variety of substituted epoxides were found to be good substrates with good regioselectivity for substitution at the less substituted side of the epoxide. A reaction using an enantioenriched secondary benzylboronic ester was found to not be stereospecific.

SUBMITTER: Gierszal SG

PROVIDER: S-EPMC8516127 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

Gierszal Sophia G SG Barker Timothy J TJ

Tetrahedron letters 20210907

A reaction between epoxides and benzylboronic acid pinacol esters is described. CuI was found to be an effective catalyst of this transformation upon activation of the benzylboronic ester with an alkyllithium reagent. The reaction was very efficient and a variety of substituted epoxides were found to be good substrates with good regioselectivity for substitution at the less substituted side of the epoxide. A reaction using an enantioenriched secondary benzylboronic ester was found to not be ster ...[more]

PMID: 34658453

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