The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantioselectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchona alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis.

The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.

The enantioselective oxidative ring-opening reaction of aziridines with α-nitroacetates has been developed. Good yields and enantioselectivity were observed for the reaction of various aziridines using a novel cinchona alkaloid amide/NiBr catalyst. Both enantiomers of products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α-aminoketones.

The catalytic enantioselective desymmetrization of aziridines with malononitrile has been developed. Good yield and enantioselectivity were obtained by using cinchona alkaloid amide/Zn(ii) catalysts. The obtained product can be converted to β-aminoester, β-aminoamide and triamide compounds.