A. Krief et al., PREPARATION AND SYNTHETIC UTILITY OF 2-METHYLSELENOMETHYL ALLYL METHYL SELENIDE - A VALUABLE PRECURSOR TO 2-SILYLMETHYLALLYLLITHIUMS, Synlett, (11), 1998, pp. 1219
3-Lithio-2-[silylmethyl]propenes, easily prepared from 3-methylseleno-
2-[silylmethyl]propenes by the cleavage of the C-Se bond, are useful i
ntermediates for the preparation of a variety of functionalised allyls
ilanes. These allylsilanes are interesting building blocks, used for e
xample, as annelating agents in the efficient synthesis of spiroketals
by the Intramolecular Silyl-Modified Sakurai (ISMS) cyclisation. The
methodology described in this article provides also an expedient route
to a range of heterosubstituted methylselenopropenes, which are valua
ble precursors to a range of useful heterosubstituted allyllithium rea
gents. Finally, a one-step preparation of functionalised allylsilanes
from readily available 3-methylseleno-2-[methylselenomethyl]propene is
reported.