Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

Jennifer R. Krumper, Walter A. Salamant, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.

Original languageEnglish (US)
Pages (from-to)4907-4910
Number of pages4
JournalOrganic Letters
Volume10
Issue number21
DOIs
StatePublished - Dec 1 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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