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Selenium-Stabilized Carbanions

  • Sylvain Ponthieux
  • Claude Paulmier
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 208)

Abstract

This chapter presents the main results published during the last ten years, concerning the generation and the reactivity of selenium-stabilized carbanions. Their formation, by α-deprotonation of selenides, selenoxides and selenones or by Se/Li exchange reactions involving selenoacetals, are mentioned. Structural aspects and carbocyclization reactions are also reported.

In a second part, the reactivity of α-phenylselanyl enolates, derived from ketones, esters, lactones and α,β-unsaturated carbonyl compounds, is discussed. Alkylation, aldolisation and Michael reactions are considered as the use of selenium-stabilized carbanions in the natural product synthesis. Others α-functionalyzed species are also presented.

In the last section, the access to a-selanyl vinylmetals is considered. Besides the classical methods involving vinylic selenides and ketene selenoacetals, the hydrometallation (M = Sn, Zr, B) of acetylenic selenides constitutes an efficient method. These species can be considered as vinyl dianion equivalents. Some examples of cross-coupling reactions are presented.

Keywords

Selenium-stabilized carbanions α-Selanyl enolates Selenides Selenoacetals Alkylation Aldolization Carbocyclization Michael addition 

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Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Sylvain Ponthieux
    • 1
  • Claude Paulmier
    • 1
  1. 1.Laboratoire de Synthèse Thio et Sélénoorganique (IRCOF)Université de Rouen, UFR SciencesMont-Saint-Aignan CedexFrance

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