173657-53-9Relevant academic research and scientific papers
Quinine as chiral discriminator for determination of enantiomeric excess of diethyl 1,2-dihydroxyalkanephosphonates
Maly, Alina,Lejczak, Barbara,Kafarski, Pawel
, p. 1019 - 1024 (2003)
Quinine was used as a 31P NMR shift reagent for the determination of the enantiomeric excess of diethyl 1,2-dihydroxyethanephosphonates obtained either by chemical or biocatalytic synthesis. Sharpless asymmetric dihydroxylation of diethyl trans
Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents
Yokomatsu, Tsutomu,Yamagishi, Takehiro,Suemune, Kenji,Yoshida, Yoshinori,Shibuya, Shiroshi
, p. 767 - 780 (2007/10/03)
Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD- mix-α or -β reagent was examined to give a series of optically active threo-α,β-dihydroxyphosphonates. Good enantioselectivity (>88% ee) was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carded out with dimethyl phosphonate instead of diethyl phosphonate.
Stereoselective synthesis of dihydroxyphosphonates via asymmetric dihydroxylation of unsaturated phosphonate esters: Synthesis of hydroxyaminophosphonates via cyclic sulfites
Lohray, B. B.,Maji, D. K.,Nandanan, E.
, p. 1023 - 1025 (2007/10/03)
Unsaturated phosphonate esters (1) have been subjected to osmium tetroxide catalyzed asymmetric dihydroxylation (AD) using dihydroquinidine and dihydroquinine derivatives as chiral ligands to furnish the optically active diols (2) which have been converte
Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
Yokomatsu,Yoshida,Suemune,Yamagishi,Shibuya
, p. 365 - 368 (2007/10/02)
The asymmetric dihydroxylation (AD) reaction of vinylphosphonates with AD-mix-α and -β reagents was successfully applied to the enantioselective synthesis of threo-α,β-dihydroxyphosphonates. β-Aryl substituents on the vinyl phosphonates were found to be good directors for the reaction with respect to the yield and enantioselectivity. The utility of chiral α,β-dihydroxyphosphonate 2c was illustrated by the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-2,2-dimethyl-5-hydroxymethyl-1,3-dioxolane 6, a potentially useful chiron for asymmetric synthesis of α-heteroatom-substituted phosphonates.
