An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

Research paper by Qing-Lan QL Pei, Guan-Da GD Che, Ru-Yi RY Zhu, Jian J He, Jin-Quan JQ Yu

Indexed on: 19 Oct '17Published on: 19 Oct '17Published in: Organic Letters


A practical method for the removal of a versatile acidic amide auxiliary has been developed. Facile alcoholysis of the amide in the presence of KOAc is enabled by an epoxide, which mechanistically resembles the removal of the Myers' auxiliary. The protocol has been applied to the removal of a variety of amide substrates and their C-H functionalization products with high efficiency and low cost, representing a step forward toward the development of a versatile directing group for C-H activation.