ol7b02841_si_001.pdf (4.65 MB)
An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary
journal contribution
posted on 2017-10-17, 16:21 authored by Qing-Lan Pei, Guan-Da Che, Ru-Yi Zhu, Jian He, Jin-Quan YuA 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.