5 years ago

An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary

An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary
Ru-Yi Zhu, Guan-Da Che, Qing-Lan Pei, Jin-Quan Yu, Jian He
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02841

DOI: 10.1021/acs.orglett.7b02841

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