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An Ir-catalyzed intramolecular asymmetric reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[ c , e ]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). This methodology represents a rare example of enantioselective chemocatalytic synthesis of chiral dibenz[ c , e ]azepines featuring a broad substrate scope, and their synthetic utilities are exhibited by derivatizing the products into a chiral amino acid derivative and chiral phosphoramidite ligands, which display excellent enantiocontrol in Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid derivatives. Remarkably, our method is also applicable to enantioselectively synthesize an allocolchicine analogue.

Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines