Kinetic Resolution of Axially Chiral 2‐Nitrovinyl Biaryls Catalyzed by a Bifunctional Thiophosphinamide

Abstract An efficient kinetic resolution of axially chiral 2‐nitrovinyl biaryls was realized through organocatalytic asymmetric Michael addition of acetone to the nitroolefin moiety. Under the catalysis of a chiral thiophosphinamide derived from (1 R ,2 R )‐1,2‐diphenylethane‐1,2‐diamine, racemic 2‐nitrovinyl biaryls were converted into highly enantiomer‐enriched 2‐nitrovinyl biaryls in 13–44% yields and a pair of separable Michael addition products bearing both axial and central chiralities in excellent stereocontrol. This represents the first successful application of asymmetric Michael addition of nitroolefins in kinetic resolution of axially chiral biaryls. magnified image