title: Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates.
abstract: Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α-amino phosphonates in excellent yields (94-97%) and diastereoselectivities (93:7-99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α-amino phosphonate into its authentic N-Cbz derivative.
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Parminder
authors.initials: P
authors.lastname: Kaur
authors.forename: Walter
authors.initials: W
authors.lastname: Wever
authors.forename: Trideep
authors.initials: T
authors.lastname: Rajale
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007097:Imines; D063065:Organophosphonates; D017905:Phosphites; D008094:Lithium