Synthesis of Azepines by a Gold-Catalyzed Intermolecular [4 + 3]-Annulation

• DOI: 10.1021/ja803890t
• Publication Date: 2008-06-25T09:01:09Z
• Authors: Nathan D. Shapiro; F. Dean Toste
• Keywords: Annulation

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