Ag. Martinez et al., Enantioselective synthesis of both enantiomers of vicinal norbornanediamines through the Leuckart reaction of 2-norbornanones, TETRAHEDR-A, 12(15), 2001, pp. 2153-2158
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.