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Synfacts 2007(8): 0863-0863  
DOI: 10.1055/s-2007-968736
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Reactions of Epoxides with LiTMP and Organolithium or Grignard Reagents

Contributor(s): Paul Knochel, Andrei Gavryushin
D. M. Hodgson*, M. J. Fleming, S. J. Stanway
University of Oxford and GlaxoSmithKline, Harlow, UK
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

The presented method is a simple and useful synthetic tool for the direct preparation of a variety of enynes, dienes, and allylsilanes from terminal epoxides, usually in highly regio- and stereoselective manner. The reactions are performed between 0 °C and ambient temperature and can be readily scaled up. This approach significantly enlarges the use of readily available epoxides as stereodefined vinyl cation equivalents.