159116-97-9Relevant academic research and scientific papers
One-Pot Two-Step Synthesis of Optically Active α-Amino Phosphonates by Palladium-Catalyzed Hydrogenation/Hydrogenolysis of α-Hydrazono Phosphonates
Goulioukina, Nataliya S.,Shergold, Ilya A.,Rybakov, Victor B.,Beletskaya, Irina P.
supporting information, p. 153 - 162 (2017/01/14)
An efficient and convenient one-pot procedure for the stereoselective catalytic synthesis of ring-substituted [amino(phenyl)methyl]phosphonates has been developed. The enantioselective hydrogenation of easily available diisopropyl (Z)-[aryl(phenylhydrazono)methyl]phosphonates using palladium(II) acetate as a precatalyst, (R)-2,2′-bis(diphenylphosphino)-5,5′-dichloro-6,6′-dimethoxy-1,1′-biphenyl [(R)-Cl–MeO-BIPHEP] as a ligand, and (1S)-(+)-10-camphorsulfonic acid as an activator in a mixture of 2,2,2-trifluoroethanol and methylene chloride at ambient temperature results in the formation of corresponding [aryl(2-phenylhydrazino)methyl]phosphonates. The subsequent cleavage of the N?N bond has been accomplished with molecular hydrogen after the addition of palladium on carbon and methanol into crude reaction mixture to afford the optically active [amino(aryl)methyl]phosphonates. The method is operationally simple and provides an appreciable enantioselectivity up to 98 % ee. (Figure presented.).
Asymmetric hydrophosphylation of chiral n-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates
Kaur, Parminder,Wever, Walter,Rajale, Trideep,Li, Guigen
experimental part, p. 314 - 319 (2011/12/22)
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 nucleophil
Chiral Br?nsted acid-catalyzed hydrophosphonylation of imines-DFT study on the effect of substituents of phosphoric acid
Akiyama, Takahiko,Morita, Hisashi,Bachu, Prabhakar,Mori, Keiji,Yamanaka, Masahiro,Hirata, Takashi
body text, p. 4950 - 4956 (2009/10/17)
The enantioselective hydrophosphonylation reaction of diisopropyl phosphite with aldimine furnished α-amino phosphonates with high enantioselectivities by means of a chiral phosphoric acid. DFT calculation of the effect of 3,3′-substituents of the phospho
Asymmetric synthesis of quaternary alpha-amino phosphonates using sulfinimines.
Davis,Lee,Yan,Titus
, p. 1757 - 1760 (2007/10/03)
The addition of lithium diethylphosphonate to enantiopure ketosulfinimines is highly diastereoselective (>95%), affording the first examples of quaternary alpha-alkyl alpha-amino (arylmethyl)phosphonates.
Enantioselective synthesis of diverse α-amino phosphonate diesters
Smith III, Amos B.,Yager, Kraig M.,Taylor, Carol M.
, p. 10879 - 10888 (2007/10/03)
An efficient, versatile protocol for the synthesis of highly enantioenriched α-amino phosphonate diesters has been devised. Addition of lithium diethyl phosphite to chiral chelating imines 31a-j, prepared from a variety of aldehydes and the chiral auxilia
