Strategic Approach to the Metamorphosis of gamma-Lactones to NH gamma-Lactams via Reductive Cleavage and C-H Amidation

Abstract

A new approach has elaborated on the conversion of gamma-lactones to the corresponding NH gamma-lactams that can serve as gamma-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH gamma-lactam building blocks starting from gamma-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.