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

摘要

We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reactionwithout any knowledge of the reaction mechanism and/or the transition-state structure, and tested thevalidity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzedreactions. A good correlation was observed between the predicted and observed E values, and thestereochemistry of the products could be predicted correctly in most cases (28 out of 30).