Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes

Laura E. Bourque, Pamela A. Haile, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

Original languageEnglish (US)
Pages (from-to)7180-7182
Number of pages3
JournalJournal of Organic Chemistry
Volume74
Issue number18
DOIs
StatePublished - Sep 18 2009

ASJC Scopus subject areas

  • Organic Chemistry

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