Domino Reactions of Tertiary Enamides in Organic Synthesis

Abstract

AbstractStudies 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 Introduction2 Strategic Considerations3 Domino Reactions of Tertiary Enamides3.1 Type I Domino Reactions3.2 Type II Domino Reactions3.3 Type III Domino Reactions4 Conclusion and Perspectives