Issue 32, 2021

Enantio- and diastereoselective double Mannich reaction of malononitrile with N-Boc imines using quinine-derived bifunctional organoiodine catalyst

Abstract

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.

Graphical abstract: Enantio- and diastereoselective double Mannich reaction of malononitrile with N-Boc imines using quinine-derived bifunctional organoiodine catalyst

Supplementary files

Article information

Article type
Communication
Submitted
24 4 2021
Accepted
26 7 2021
First published
27 7 2021

Org. Biomol. Chem., 2021,19, 6969-6973

Enantio- and diastereoselective double Mannich reaction of malononitrile with N-Boc imines using quinine-derived bifunctional organoiodine catalyst

S. Kuwano, E. Ogino and T. Arai, Org. Biomol. Chem., 2021, 19, 6969 DOI: 10.1039/D1OB00796C

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