Catalytic Enantioselective Desymmetrization of meso-Diamines

Significance

Seidel and De report the first catalytic enantioselective desymmetrization of meso-1,2-diaryl-1,2-diaminethanes by monobenzoylation catalyzed by a combination of DMAP and a chiral amido-thiourea. The reaction scope shows that substrates with electron-withdrawing and -donating groups at different positions on the aromatic ring led to the desymmetrization products in moderate to good yield and with good enantioselectivity. The products of diacylation have not been observed. The authors add value to their work with the synthesis of urea and thiourea compounds with good enantioselectivities.