Intramolecular anti-hydrosilylation and silicon-assisted cross-coupling: Highly regio- and stereoselective synthesis of trisubstituted homoallylic alcohols

Scott E. Denmark, Weitao Pan

Research output: Contribution to journalArticlepeer-review

Abstract

(Formula Presented) A highly regio- and stereoselective anti-intramolecular hydrosilylation of alkynyl silyl ethers catalyzed by a ruthenium arene complex has been developed. The resultant (Z)-alkylidenesilacyclopentanes are efficiently coupled with aryl or alkenyl halides in the presence of tetrabutylammonium fluoride and a palladium(0) catalyst. The yields are generally good, and the reaction is compatible with a wide range of functional groups. The overall transformation achieves the stereoselective conversion of homopropargyl alcohols to trisubstituted homoallylic alcohols.

Original languageEnglish (US)
Pages (from-to)4163-4166
Number of pages4
JournalOrganic Letters
Volume4
Issue number23
DOIs
StatePublished - Nov 14 2002

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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