Methyllithium-promoted Wittig rearrangements of alpha-alkoxysilanes.
[formula: see text] The Wittig rearrangements of alpha-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 alpha to the silane. Furthermore the sigmatropic shifts can often be followed by other synthetically useful in situ chemical events.
Maleczka
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Department of Chemistry, Michigan State University, East Lansing 48824, USA. maleczka@cem.msu.edu
Geng
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D000473:Alkanes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
D000473:Alkanes; D012821:Silanes; D008094:Lithium