Issue 28, 2015

Exploring tertiary enamides as versatile synthons in organic synthesis

Abstract

Tertiary enamides have long been thought of as stable and marginally valuable enamine variants in synthesis. This notion has been challenged, however, in recent years. Enabling the regulation of the cross-conjugation system of the tertiary enamides has been successfully shown to enhance delocalization of the nitrogen lone-pair electrons into a carbon–carbon double, thereby reinvigorating the enaminic reactivity of the tertiary enamides. In this article, I summarize the recent advances in the exploration of the nucleophilic reactions of tertiary enamides and their applications in the synthesis of natural products and heterocyclic compounds of biological and pharmaceutical relevance, with a primary focus on our own work.

Graphical abstract: Exploring tertiary enamides as versatile synthons in organic synthesis

Article information

Article type
Feature Article
Submitted
26 Dec 2014
Accepted
27 Jan 2015
First published
27 Jan 2015

Chem. Commun., 2015,51, 6039-6049

Exploring tertiary enamides as versatile synthons in organic synthesis

M. Wang, Chem. Commun., 2015, 51, 6039 DOI: 10.1039/C4CC10327K

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