Methyllithium-Promoted Wittig Rearrangements of α-Alkoxysilanes

Robert E. Maleczka, Jr.,* and Feng Geng
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824
Org. Lett., 1999, 1 (7), pp 1115–1118
DOI: 10.1021/ol990912+
Publication Date (Web): September 16, 1999
Copyright © 1999 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, maleczka@cem.msu.edu

Abstract

Abstract Image

The Wittig rearrangements of α-alkoxysilanes, promoted by the action of methyllithium were studied. Depending on both the substrate and reaction conditions employed, [2,3]-, [1,2]-, or [1,4]-Wittig rearrangements can be realized. These rearrangements were shown to be initiated by either Si/Li exchange or deprotonation α to the silane. Furthermore the sigmatropic shifts can often be followed by other synthetically useful in situ chemical events.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue October 07, 1999
  • Received August 5, 1999

Recommend & Share

Related Content

Other ACS content by these authors: