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Synthesis 2008(15): 2307-2317
DOI: 10.1055/s-2008-1067173
DOI: 10.1055/s-2008-1067173
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
The Phosphine-Catalyzed Alkyne to 1,3-Diene Isomerization Reaction
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
Key words
organocatalysis - isomerization reactions - phosphines - alkynes - 1,3-dienes