NADH Models in the Pyrrolo[3,4-b]pyridine Series. Role of the Cyclized Structure in the Stereocontrol of Reductions

The synthesis of a chiral NADH model in pyrrolo[3,4-b]pyridine series is described and the asymmetric reduction of methyl benzoylformate is studied. Its asymmetric behavior compared with a cyclized analogue in naphthyridine series suggests that the orientation of the carbonyl group of the lactam plays an important role in the stereochemical control of the reduction.