Domino Reactions of Tertiary Enamides in Organic Synthesis

Abstract

Studies in recent decade have shown that tertiary enamides, once thought of as unreactive and marginally useful enamine variants, are shelf-stable yet versatile nucleophilic intermediates in organic synthesis. Many compounds, especially N-heterocycles, have been synthesized by monofunctionalization reactions of tertiary enamides. By taking advantage of intramolecular and intermolecular interception of the putative acyliminium intermediates formed by the initial nucleophilic reactions of tertiary enamides, we have established several novel difunctionalization reaction methods for constructing diverse complex fused heterocyclic products. In this Account, we summarize our endeavors to develop difunctionalization reactions of tertiary enamides in a domino fashion.

1 Introduction

2 Strategic Considerations

3 Domino Reactions of Tertiary Enamides

3.1 Type I Domino Reactions

3.2 Type II Domino Reactions

3.3 Type III Domino Reactions

4 Conclusion and Perspectives

Key words

enamides - domino reaction - nucleophilic addition - asymmetric synthesis - N-heterocycles - alkaloids

Publication History

Received: 29 December 2020

Accepted after revision: 13 January 2021

Accepted Manuscript online:
13 January 2021

Article published online:
02 February 2021

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