Kinetic resolution of BINAMs by stereoselective Copper-catalyzed dehydrogenative Si–N coupling with prochiral dihydrosilanes

A nonenzymatic kinetic resolution of monoprotected 1,1′-binaphthyl-2,2′-diamine (BINAM) derivatives is reported. This is achieved by a Cu–H-catalyzed dehydrogenative Si–N coupling with prochiral dihydrosilanes using (R,R)-Ph-BPE as a chiral ligand. The atroposelective as well as diastereoselective N-silylation enables the resolution of BINAMs with various substituents in 6,6′- or 7,7′-positions with good to synthetically useful selectivity factors.