Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors

Wing Ki Chung, Sze Kui Lam, Brian Lo, Lok Lok Liu, Wing Tak Wong, Pauline Chiu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

63 Citations (Scopus)

Abstract

Using epoxy enol triethylsilanes as oxyallyl cation precursors, [4 + 3] cycloadditions with various dienes occur under catalysis by silyl triflates and acids in good yields. The intramolecular [4 + 3] cycloaddition proceeds under mild conditions and generate hydroxylated cycloadducts with high diastereoselectivity and yields. Enantiomerically pure epoxy enol silanes have been shown to give excellent yields of the optically pure cycloadduct bearing multiple stereocenters.
Original languageEnglish
Pages (from-to)4556-4557
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number13
DOIs
Publication statusPublished - 8 Apr 2009
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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