Enantioselective Oxidative Coupling of β-Ketocarbonyls and Anilines by Joint Chiral Primary Amine and Selenium Catalysis.

Abstract

An enantioselective primary amine-catalyzed total N-selective nitroso aldol reaction (N-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% H2O2. This protocol provides a facile and highly efficient access to α-hydroxyamino carbonyls bearing chiral quaternary centers under exceedingly mild and green reaction conditions with high chemo- and enantiocontrol.