title: Room-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to maleimides and enones in the presence of CF3-substituted MeOBIPHEP analogues.
abstract: A Rh-based catalytic system implying electron-poor MeOBIPHEP analogues has been developed for the 1,4-addition of boronic acids to maleimides and enones under mild conditions at room temperature and led to succinimide derivatives and arylated cyclic ketones in good to excellent yields and ee. We uncovered the crucial role of the electronic and steric properties of diphosphine ligand and observed a strong boronic acid/ligand dependency in the case of maleimide derivatives and substrate/ligand matching in the case of cyclic enones.
authors: Chimie ParisTech UMR 7223, Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75231 Paris Cedex 05, France.
authors: Florent
authors: F
authors: Le Boucher d'Herouville
authors: Anthony
authors: A
authors: Millet
authors: Michelangelo
authors: M
authors: Scalone
authors: Véronique
authors: V
authors: Michelet
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D001555:Benzene Derivatives; D001897:Boronic Acids; D008024:Ligands; D008301:Maleimides; D009943:Organophosphorus Compounds; D010720:Phosphines; C043592:maleimide; D012238:Rhodium