Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

Tadashi Ema, Norichika Ura, Masataka Yoshii, Toshinobu Korenaga, Takashi Sakai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

Original languageEnglish
Pages (from-to)9583-9591
Number of pages9
JournalTetrahedron
Volume65
Issue number46
DOIs
Publication statusPublished - Nov 14 2009

Keywords

  • Enantioselectivity
  • Lipase
  • Oxazaborolidine
  • Prediction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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