Volume 2009, Issue 12 p. 1831-1844
Microreview

Mechanistic Manifold and New Developments of the Julia–Kocienski Reaction

Christophe Aïssa

Christophe Aïssa

Department of Chemistry, University of Liverpool, Crown Street, L69 7ZD, Liverpool, England

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First published: 30 March 2009
Citations: 238

Graphical Abstract

The olefination toolbox, already well fitted with heterocyclic sulfones, has recently been further enriched with new electron-poor sulfones. Moreover, results garnered over the past two decades seem to confirm the mechanistic assumptions put forward by S. Julia since his seminal discovery of the Julia–Kocienski olefination.

Abstract

The Julia–Kocienski reaction has become indispensable in the synthetic organic chemist's olefination toolbox. Although the stereochemical outcome of the transformation is sometimes difficult to predict, some trends can be explained by an array of mechanistic hypotheses which have been put forward since the initial disclosure of the reaction. Moreover, several important developments have been recently reported and are summarised in this microreview. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)