Enantioselective synthesis of both enantiomers of vicinal norbornanediamines through the Leuckart reaction of 2-norbornanones

The reaction of 2-norbornanones bearing an amine derivative in the bridgehe ad position with formamide and formic acid yields enantiomerically pure 1,2 -norbornane diamides. These compounds are excellent precursors of chiral vi cinal diamines, which have been increasingly used due to their numerous app lications in medicinal chemistry and asymmetric synthesis. The rigid struct ure of the norbornane framework allows the study of conformational equilibr ium in the formamide groups and its dependence on other substituents in the molecule. (C) 2001 Published by Elsevier Science Ltd.