Enantioselective addition of nitromethane to alpha-keto esters catalyzed by copper(II)-iminopyridine complexes.
The copper complex of a chiral iminopyridine easily prepared from (R)-(-)-fenchone and picolylamine catalyzes the enantioselective Henry (nitroaldol) reaction between nitromethane and alpha-keto esters. Good yields and modest to good enantioselectivities are obtained for a wide range of alpha-keto esters, bearing aromatic, alkyl or alkenyl groups attached to the ketone carbonyl group.
Blay
Gonzalo
G
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100-Burjassot, València, Spain. gonzalo.blay@uv.es
Hernández-Olmos
Victor
V
Pedro
José R
JR
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004952:Esters; D008024:Ligands; D009595:Nitroparaffins; D011725:Pyridines; D003300:Copper; D008697:Methane; C008640:nitromethane