Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

Article abstract of DOI:10.1016/S0040-4020(97)10294-0

The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics 1a and 1b were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with 1a proceeded with high stereoselectivity in both substrates, while 1b showed much lower chirality transfer.