Oxazaborolidine mediated asymmetric ketone reduction: prediction of enantiomeric excess based on catalyst structure

The feasibility of enantiomeric excess (ee) prediction is demonstrated for asymmetric oxazaborolidine mediated ketone reduction. A quantitative structure-selectivity (QSSR) model of chiral oxazaborolidines was created by using multivariate data analysis. High-throughput methods and regression techniques were used to correlate the model with the ee's of reactions with a training set and to predict the ee's for an additional set of oxazaborolidines. The predicted ee's corresponded well with the actual values, indicating that the model is very useful for the initial selection of catalysts for screening experiments. (C) 2003 Elsevier Ltd. All rights reserved.