Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

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

Research output: Contribution to journalArticlepeer-review


(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
Issue number21
StatePublished - 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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