Synthesis of α-chiral amides via synergistic visible-light-induced Wolff rearrangement and asymmetric NHC catalysis

Abstract

Herein, a visible-light-induced chiral N-heterocyclic carbene (NHC)-catalyzed asymmetric amination of ketenes has been developed. This strategy provides a convenient and facile synthetic protocol for the efficient construction of α-chiral amides under mild reaction conditions with moderate to excellent yields and stereoselectivities (up to 95% yields and 97 : 3 e.r.). Furthermore, a chiral 2-phenyl-1-propylamine derivative and (R)-ibuprofen could be obtained after simple transformations of the chiral products.