title: Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.
abstract: C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation with (-)-quinine, and subsequent fractional crystallization. X-ray crystallographic analysis of one of the diastereomeric salts clearly revealed that (-)-quinine could be an efficient resolving agent for obtaining the single enantiomer (R,R)-N,N-bis(phosphinomethyl)amine.
authors.affiliation: Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan, Iran.
authors.forename: Babak
authors.initials: B
authors.lastname: Kaboudin
authors.forename: Mohammad Reza
authors.initials: MR
authors.lastname: Faghihi
authors.forename: Foad
authors.initials: F
authors.lastname: Kazemi
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Yokomatsu
mesh_terms: D000588:Amines / Q000737:chemistry*; D008958:Models, Molecular; D010721:Phosphinic Acids / Q000737:chemistry*; D011803:Quinine / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D010721:Phosphinic Acids; D012492:Salts; D011803:Quinine
keywords: C2-symmetric; thermal reaction; α-aminophosphinic acids