Asymmetric Multicomponent Sulfa-Michael/Mannich Cascade Reaction: Synthetic Access to 1,2-Diamino-3-Organosulfur Compounds and 2‑Nitro Allylic Amines

A novel catalytic asymmetric three-component
intermolecular sulfa-Michael/Mannich
cascade reaction has been developed using a chiral multifunctional
catalyst. This reaction provides facile access to 1-amino-2-nitro-3-organosulfur
compounds bearing three consecutive stereocenters in high yields (up
to 96%) with good diastereo- (up to 91:4:4:1 dr)
and excellent enantioselectivities (93–99% ee). Furthermore, the products of this reaction could be facilely transformed
into potentially bioactive 1, 2-diamino-3-organosulfur compounds and
2-nitro allylic amines.