Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines

Abstract

A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can be isolated through an enantioselective oxidative dearomatization in up to 92% yield and 97% ee. The further synthetic utility of the optically enriched spirooxazolines was examined providing a corresponding 2-naphthalenole and an oxepin.