RATIONAL DE-NOVO DESIGN OF NADH MIMIC FOR STEREOSELECTIVE REDUCTION BASED ON MOLECULAR-ORBITAL CALCULATION

The methodology of rational design of NADH mimics in stereoselective r eduction of carbonyl and imino groups based on molecular orbital calcu lation was described. The designed NADH mimics la and Ib were subjecte d to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, whi le Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.