title: Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides.
abstract: A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620, USA.
authors.forename: Gajendrasingh K
authors.initials: GK
authors.lastname: Ingle
authors.forename: Yuxue
authors.initials: Y
authors.lastname: Liang
authors.forename: Michael G
authors.initials: MG
authors.lastname: Mormino
authors.forename: Guilong
authors.initials: G
authors.lastname: Li
authors.forename: Frank R
authors.initials: FR
authors.lastname: Fronczek
authors.forename: Jon C
authors.initials: JC
authors.lastname: Antilla
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; C406944:BINOL, naphthol; D007097:Imines; D009284:Naphthols; D009943:Organophosphorus Compounds; D010087:Oxides; D010720:Phosphines; C044646:phosphine; D008274:Magnesium