A parallel preparation of a bicyclic N-chiral amine library and its use for chiral catalyst screening

A parallel library of optically active bicyclic tertiary amines bearing N-chiral bridgehead nitrogen atoms was readily prepared by condensation of primary amines, cyclic amino acids and aldehydes. The enantiocontrolling ability of each of the library members was examined for the asymmetric alkylation of benzaldehyde with diethylzinc, and (3R,6R,7aS)-(2,3-diphenyl-6-hydroxy)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one, which contains a β-amino alcohol unit, showed high enantioselectivity.