Enantioselective addition of various aryllithium reagents to aromatic imines was catalyzed (20 mol-%) by readily accessible 1,2-diamines to afford a wide range of protected diarylmethylamines in up to 94 % enantiomeric excess. Furthermore, the absolute configuration of these arylation products was determined by using X-ray crystallography
Imines. -An efficient arylation of aromatic imines uses a wide diversity of aryllithium reagents activated by chiral 1,2-diamines CDA-1 and CDA-2. Two equivalents of ligand are necessary to obtain good yields and enantioselectivities. However, in some cases substoichiometric amounts (20 mol%) are sufficient to afford diarylmethylamines in up to 94% e.e. By simply changing the imine/organolithium partner, either enantiomer can be produced [cf. (IIIc)]. The absolute configuration of product (VIII) could be established. -(CABELLO, N.; KIZIRIAN, J.-C.; GILLE, S.; ALEXAKIS*, A.; BERNARDINELLI, G.; PINCHARD, L.; CAILLE, J.-C.; Eur.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.