Reactions of Epoxides with LiTMP and Organolithium or Grignard Reagents

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.