Rational design of novel axially chiral NADH models based on configurational control of atropisomeric lactams

The preparation of a new class of axially chiral NADH models based on confi gurational control of atropisomeric lactams is described. The configuration al control of this chiral axis is achieved via the presence of a second chi rality element installed on the lactam moiety of the reagent 2. Reduction o f methyl benzoylformate led to methyl mandelate in 89% yield and 92% e.e. T his result suggests that the chiral axis about C3 C=O bond is the main conf igurational element responsible for the high enantioselectivity observed wi th this biomimetic model. (C) 2001 Elsevier Science Ltd. All rights reserve d.