Enantioselective Mannich Reaction Promoted by Chiral Phosphinoyl-Aziridines

Abstract

In this study, a set of enantiomerically pure aziridines bearing a phosphine oxide moiety were prepared in high yields and tested as chiral catalysts in the direct asymmetric Mannich reaction of hydroxyacetone, an amine (p-anisidine), and various aromatic aldehydes. The appropriate Mannich adducts were formed in chemical yields from moderate to good with a high level of enantio- and diastereoselectivity. The best results were obtained using the catalysts bearing a free NH-aziridine subunit.

Keywords

• asymmetric synthesis
• aziridines
• mannich reaction
• organocatalysis