Alkylidenesilacyclopropanes derived from allenes: Applications to the selective synthesis of triols and homoallylic alcohols

Kay M. Buchner, Timothy B. Clark, Janice M.N. Loy, Thong X. Nguyen, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

Several alkylidenesilacyclopropanes were prepared by silver-mediated silylene transfer to allenes. Oxasilacyclopentanes derived from allenes were prepared with high regio- and diastereoselectivity by a two-step, one-flask silacyclopropanation/carbonyl insertion reaction. Triols and homoallylic alcohols were formed diastereoselectively by functionalizing the oxasilacyclopentanes. An optically active allene (>98% ee) was utilized to synthesize an enantiopure homoallylic alcohol in 96% ee.

Original languageEnglish (US)
Pages (from-to)2173-2175
Number of pages3
JournalOrganic Letters
Volume11
Issue number10
DOIs
StatePublished - May 21 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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