Catalytic Mannich-type reactions of α-aminoacetonitrile using fluorenylidene as a protecting and activating group

Catalytic Mannich-type reactions of 9-fluorenylidene-protected α-aminoacetonitrile with imines were investigated. The desired reactions proceeded smoothly to afford the Mannich-type adducts in high yields with high diastereoselectivities in the presence of a catalytic amount of 1,1,3,3-tetramethylguanidine (TMG). A chiral guanidine catalyzed the reaction with good enantioselectivity.