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

Jared T. Shaw, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

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
  • Drug Discovery
  • Organic Chemistry

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