Gold-Catalyzed N,O-Functionalizations of 6-Allenyl-1-ynes with N-Hydroxyanilines To Construct Benzo[b]-azepin-4-one Cores

Org Lett. 2017 Oct 6;19(19):5340-5343. doi: 10.1021/acs.orglett.7b02629. Epub 2017 Sep 26.

Abstract

Gold-catalyzed reactions of 6-allen-1-ynes with N-hydroxyanilines afford thermally stable benzoazepin-4-ones in anti-selectivity; these anti-configured products are easily isomerized to their syn-isomers on a silica column. The mechanism of reactions likely involve initial nitrone/allene cycloadditions, followed by skeletal rearrangement of resulting intermediates.

Publication types

  • Research Support, Non-U.S. Gov't