Highly Effective Asymmetric Henry Reaction Catalyzed by Chiral Aziridine-Functionalized Organophosphorus Compounds

Remaining in the research topic related to the discovery of new catalytic abilities of chiral organophosphorus derivatives of aziridines, we decided to synthesize organophosphorus compounds containing an aziridine ring, previously described by our group, and to investigate their catalytic activity in the asymmetric nitroaldol (Henry) reaction between aromatic aldehydes and nitromethane in the presence of catalytic amounts of copper (II) acetate. In some cases, the chiral β-nitroalcohols obtained with high chemical yield were characterized by very high values ​​of enantiomeric excess (over 95%). What is quite important, the use of two enantiomerically pure catalysts differing in the absolute configuration of the aziridine unit led to the formation of two enantiomeric products of the Henry reaction.