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Preparation and synthetic utility of 2-methylselenomethyl allyl methyl selenide. A valuable precursor to 2-silylmethylallyllithiums

  • A. Krief
  • , W. Dumont
  • , I.E. Markó
  • , F. Murphy
  • , J.-C. Vanherck
  • , R. Duval
  • , T. Ollevier
  • , U. Abel

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)1219-1222
Number of pages4
JournalSynlett
Issue number11
Publication statusPublished - 1 Nov 1998

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