Methyllithium-Promoted Wittig Rearrangements of α-Alkoxysilanes
Robert E. Maleczka, Jr.* and Feng Geng
*Department of Chemistry, Michigan State University, East Lansing, Michigan
48824, Email: maleczka
cem.msu.edu
R. E. Maleczka, Jr., F. Geng, Org. Lett., 1999, 1, 1115-1118.
DOI: 10.1021/ol990912+
Abstract
Depending on both the substrate and reaction conditions employed, α-alkoxysilanes underwent [2,3]-, [1,2]-, or [1,4]-Wittig rearrangements promoted by the action of methyllithium. These rearrangements were shown to be initiated by either Si/Li exchange or deprotonation to the silane.
see article for more reactions
proposed mechanism
Synthesis and Fluoride-Promoted Wittig Rearrangements of α-Alkoxysilanes
R. E. Maleczka, Jr., F. Geng, Org. Lett., 1999, 1, 1111-1113.
Key Words
[1,2]-Wittig Rearrangement, [2,3]-Wittig Rearrangement
ID: J54-Y1999-500
