Oxidative coupling of enolates, enol silanes, and enamines: Methods and natural product synthesis

Fenghai Guo, Michael D. Clift, Regan J. Thomson*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

91 Scopus citations

Abstract

Oxidative coupling of enolates, enol silanes, and enamines provides a direct method for the construction of useful 1,4-dicarbonyl synthons. Despite its first being reported in 1935, with subsequent important advances beginning in the 1970s, the development of this powerful reaction into a reliable methodology was somewhat limited. In recent years, though, there have been a number of reports from several research groups demonstrating advances in several neglected areas of oxidative coupling. This microreview summarizes these new advances in methodology and provides an overview of recent natural product syntheses that showcase the power of these transformations. Recent years have seen the development of several new methods for the oxidative coupling of enolates and related derivatives. This microreview summarizes some key methodology addressing issues of cross-coupling and stereocontrol. The utility of oxidative enolate coupling is highlighted by descriptions of recent strategic applications of the reaction in natural product total synthesis.

Original languageEnglish (US)
Pages (from-to)4881-4896
Number of pages16
JournalEuropean Journal of Organic Chemistry
Issue number26
DOIs
StatePublished - Sep 1 2012

Keywords

  • C-C coupling
  • Enols
  • Natural products
  • Oxidative coupling
  • Synthesis design

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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