Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations

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Abstract

The origins of the high enantioselectivity of chiral phosphoric acid-catalyzed oxetane desymmetrizations were investigated by density functional theory (DFT) calculations. Distortion of the catalyst structure, caused by steric crowding in the catalyst pocket of one enantiomeric transition state, is the main cause for stereochemical preference. A general model was developed to assist in the rational design of new catalysts for related transformations.

Original languageEnglish (US)
Pages (from-to)12356-12359
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number38
DOIs
StatePublished - Sep 28 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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