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DOI: 10.1055/s-0029-1218558
Strategies for Heterocyclic Synthesis via Cascade Reactions Based on Ketenimines
Publication History
Publication Date:
10 December 2009 (online)
Abstract
The development of highly efficient methodologies for constructing heterocyclic compounds is a major challenge in organic chemistry. This Account presents the recent progresses on cascade strategies for heterocyclic synthesis based on ketenimine intermediates. Three types of cascade reactions for the synthesis of a variety of heterocycles, involving nucleophilic addition to the central carbon of ketenimine, radical addition to the central carbon of ketenimine, and pericyclic reaction of ketenimine, are highlighted in this Account. A brief discussion on the mechanism of copper-catalyzed azide-alkyne cycloaddition (CuAAC) providing ketenimines is also included.
1 Introduction
2 Nucleophilic Addition to the Central Carbon of Ketenimines
3 Radical Addition to Ketenimines
4 Pericyclic Reactions of Ketenimines: Cycloaddition Reaction
4.1 Ketenimine-Imine [2+2] Cycloadditions
4.2 Ketenimine-Alkene [2+2] Cycloadditions
5 Pericyclic Reactions of Ketenimines: Electrocyclic Ring Closure
6 Pericyclic Reactions of Ketenimines: Sigmatropic Migration
7 Conclusions and Outlook
Key words
ketenimine - cascade reaction - heterocyclic compound - nucleophilic addition - radical addition - cycloaddition - electrocyclic ring closure - sigmatropic migration
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