Satoru Kuwano, Eri Ogino and Takayoshi Arai
Org. Biomol. Chem., 2021,19, 6969-6973
DOI:
10.1039/D1OB00796C,
Communication
A chiral quinine-derived organic base catalyst with halogen bond donor functionality was used to catalyze the asymmetric double Mannich reaction of malononitrile with N-Boc and N-Cbz imines to afford 1,3-diamines in excellent yields with high enantio- and diastereoselectivities. With 2.2 equiv. of a single imine electrophile, symmetrical 1,3-diamines were obtained, whereas, with two different imine partners, unsymmetrically substituted 1,3-diamine was obtained. The monohydration of the double Mannich product was also achieved.