Preparation and synthetic utility of 2-methylselenomethyl allyl methyl selenide. A valuable precursor to 2-silylmethylallyllithiums
(1998) Synlett : accounts and rapid communications in synthetic organic chemistry — n° 11, p. 1219-+ (1998)
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- Abstract
- 3-Lithio-2-[silylmethyl]propenes, easily prepared from 3-methylseleno-2-[silylmethyl]propenes by the cleavage of the C-Se bond, are useful intermediates for the preparation of a variety of functionalised allylsilanes. These allylsilanes are interesting building blocks, used for example, 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 valuable precursors to a range of useful heterosubstituted allyllithium reagents. Finally, a one-step preparation of functionalised allylsilanes from readily available 3-methylseleno-2-[methylselenomethyl]propene is reported.
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Krief, A., Dumont, W., Marko, I., Murphy, F., Vanherck, JC., Duval, R., Ollevier, T., & Abel, U. (1998). Preparation and synthetic utility of 2-methylselenomethyl allyl methyl selenide. A valuable precursor to 2-silylmethylallyllithiums. Synlett : accounts and rapid communications in synthetic organic chemistry, 11, 1219-+. https://doi.org/10.1055/s-1998-1915 (Original work published 1998)