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An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

ABSTRACT: 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.

SUBMITTER: Pei QL

PROVIDER: S-EPMC5710756 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

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

Organic letters 20171101 21

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. ...[more]

PMID: 29039962

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