REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALLYLTRIMETHYLSILANES VIA KRIEF-REICH ELIMINATION IN β-SELENO-γ-SILYL ALCOHOLS

Article abstract of DOI:10.1016/S0040-4020(01)89757-X

The synthesis of (E)-allyltrimethylsilanes by regio- and stereocontrolled pathways is described based on the preference for Krief-Reich elimination over silicon-controlled rearrangement in β-seleno-γ-silyl alcohols, readily available from α-selenoaldehydes, 10 - 12.Usefulness of this protocol for the introduction of the allylsilane function α to the carbonyl group in cycloalkanones as well as for the preparation of unsymmetrically substituted allylsilanes is also reported.