Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes

Brian Lo, Sarah Lam, Wing Tak Wong, Pauline Chiu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

41 Citations (Scopus)

Abstract

A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl).
Original languageEnglish
Pages (from-to)12120-12123
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number48
DOIs
Publication statusPublished - 26 Nov 2012
Externally publishedYes

Keywords

  • allylic compounds
  • cycloaddition
  • heterocycles
  • stereoselectivity
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this