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

Org Lett. 2009 May 21;11(10):2173-5. doi: 10.1021/ol900456v.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Alkadienes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Molecular Structure
  • Silanes / chemical synthesis*
  • Silanes / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Alkadienes
  • Cyclopropanes
  • Silanes
  • propadiene