The Phosphine-Catalyzed Alkyne
to 1,3-Diene Isomerization Reaction

Cathy Kar-Wing Kwong; Michael Yunyi Fu; Cynthia Sze-Lok Lam; Patrick H. Toy

doi:10.1055/s-2008-1067173

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Synthesis 2008(15): 2307-2317
DOI: 10.1055/s-2008-1067173

REVIEW

The Phosphine-Catalyzed Alkyne to 1,3-Diene Isomerization Reaction

Cathy Kar-Wing Kwong, Michael Yunyi Fu, Cynthia Sze-Lok Lam, Patrick H. Toy*
Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
Fax: +85228571586; e-Mail: phtoy@hku.hk;

Further Information

Publication History

Received 13 February 2008
Publication Date:
08 July 2008 (online)

Abstract
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Abstract

The alkyne to 1,3-diene isomerization reaction is a process in which a nucleophilic phosphine catalyst promotes the rearrangement of an electron-withdrawing group activated alkyne to the corresponding conjugated diene. The origin, mechanism, development, and application of this organocatalytic and stereoselective reaction in the synthesis of complex organic molecules are reviewed.

1 Introduction

2 The Reaction

2.1 Background

2.2 Mechanism

2.3 Development

2.4 Synthetic Applications

3 Conclusions

Key words

organocatalysis - isomerization reactions - phosphines - alkynes - 1,3-dienes

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The August 2004 issues of both Adv. Synth. Catal. and Acc. Chem. Res., the January 9, 2006 issue of Tetrahedron, and the December 2007 issue of Chem. Rev. are dedicated to the topic of organocatalysis.