Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: Trichloroethylene as solvent for stereoselective C - And O-glycosylations

Joanna C. Kendale, Elizabeth M. Valentín, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of SN1 products, while nonpolar solvents favor SN2 products. Trichloroethylene was identified as the solvent most likely to give SN2 products in both C- and O-glycosylation reactions.

Original languageEnglish (US)
Pages (from-to)3684-3687
Number of pages4
JournalOrganic Letters
Volume16
Issue number14
DOIs
Publication statusPublished - Jul 18 2014

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ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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