Evaluation of the Chiral DIANANE Backbone as Ligand for Organolithium Reagents

Novel endo,endo-2,5-diaminonorbonane-derived tertiary C2-symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines.