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Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation.

ABSTRACT: A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate.

SUBMITTER: Shapiro ND

PROVIDER: S-EPMC2754784 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation.

Shapiro Nathan D ND Toste F Dean FD

Journal of the American Chemical Society 20080625 29

A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate. ...[more]

PMID: 18576648

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