Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

Jared T. Shaw, K. A. Woerpel

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2- methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate.

Original languageEnglish (US)
Pages (from-to)8747-8756
Number of pages10
JournalTetrahedron
Volume55
Issue number29
DOIs
StatePublished - Jul 16 1999

Keywords

  • Carbenium ions
  • Furans

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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