Synthesis 2008(15): 2307-2317  
DOI: 10.1055/s-2008-1067173
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

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)

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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