4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 29, Pages 9244-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja803890t

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Funding

  1. NIGMS NIH HHS [R01 GM073932-04, R01 GM073932] Funding Source: Medline

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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.

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