Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst

Org Lett. 2004 Feb 19;6(4):625-7. doi: 10.1021/ol0364531.

Abstract

[reaction: see text] The aza-Henry reaction of imines with nitroalkanes was promoted by chiral thiourea with an N,N-dimethylamino group to give beta-nitroamines with good enantioselectivity. Various N-protected imines were examined as substrates. N-Phosphinoylimine gave the best result in terms of chemical yield and enantioselectivity (up to 91% yield, up to 76% ee).