title: New multifunctional chiral phosphines and BINOL derivatives co-catalyzed enantioselective aza-Morita-Baylis-Hillman reaction of 5,5-disubstituted cyclopent-2-enone and N-sulfonated imines.
abstract: New multifunctional chiral phosphine (phosphine-amide type) LB8 and BINOL derivative co-catalyzed asymmetric aza-MBH reaction of 5,5-disubstituted cyclopent-2-enones with N-sulfonated imines afforded the corresponding optically active adducts in good to outstanding yields with moderate to good ee's under mild conditions. The steric hindrance environment of BINOL derivatives as well as the nucleophilicity of the phosphorus center and the acidity of free OH which could significantly affect the stereochemical and chemical outcomes had been discussed, indicating the co-catalyzed system is very important to this particular asymmetric aza-MBH reaction.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, China.
authors.forename: Yuan-Liang
authors.initials: YL
authors.lastname: Yang
authors.forename: Yin
authors.initials: Y
authors.lastname: Wei
authors.forename: Min
authors.initials: M
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C406944:BINOL, naphthol; D003517:Cyclopentanes; D007097:Imines; D007659:Ketones; D009284:Naphthols; D010720:Phosphines