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Issue 8, 2020
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γ-C (sp3)–H bond functionalisation of α,β-unsaturated amides through an umpolung strategy

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Abstract

The nucleophilic γ-phenylation and γ-alkylation of α,β-unsaturated amides have been developed. This umpolung reaction allows the regioselective introduction of phenyl and alkyl groups to a vinylketene N,O-acetal, which is generated in situ from an α,β-unsaturated N-alkoxyamide, followed by N–O bond cleavage in a two-step, one-pot process.

Graphical abstract: γ-C (sp3)–H bond functionalisation of α,β-unsaturated amides through an umpolung strategy

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Article information


Submitted
20 Jan 2020
Accepted
01 Feb 2020
First published
03 Feb 2020

Org. Biomol. Chem., 2020,18, 1563-1566
Article type
Communication

γ-C (sp3)–H bond functionalisation of α,β-unsaturated amides through an umpolung strategy

E. Futaki, N. Takeda, M. Yasui, T. Shinada, O. Miyata and M. Ueda, Org. Biomol. Chem., 2020, 18, 1563
DOI: 10.1039/D0OB00125B

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