97995-93-2Relevant academic research and scientific papers
[5.5]-P-spirocyclic chiral triaminoiminophosphorane-catalyzed asymmetric hydrophosphonylation of aldehydes and ynones daisuke uraguchi1
Ito, Takaki,Kimura, Yuto,Nobori, Yumiko,Sato, Makoto,Ooi, Takashi
, p. 546 - 555 (2017)
Development of highly efficient and enantioselective hydrophosphonylations of aldehydes and ynones mediated by [5.5]- P-spirocyclic chiral triaminoiminophosphoranes as base catalysts is described. The strong basicity of the iminophosphoranes and hydrogen-
Asymmetric synthesis of α-hydroxy-phosphonamides, phosphonates and phosphonic acids
Blazis,Koeller,Spilling
, p. 499 - 502 (1994)
The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54-93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane
Evidence for substrate binding by the lanthanide centers in [Li 3(thf)n(binolate)3Ln]: Solution and solid-state characterization of seven- and eight-coordinate [Li3(sol) n(binolate)3Ln(S)
Wooten, Alfred J.,Carroll, Patrick J.,Walsh, Patrick J.
, p. 2549 - 2552 (2006)
(Chemical Equation Presented) A close bond: The heterobimetallic complexes [M3(thf)n(binolate)3Ln] (M = Li, Na, K) are among the most effective asymmetric Lewis acid catalysts. Previous solution and solid-state studies pro
Insight into substrate binding in Shibasaki's Li3(THF) n(BINOLate)3Ln complexes and implications in catalysis
Wooten, Alfred J.,Carroll, Patrick J.,Walsh, Patrick J.
, p. 7407 - 7419 (2008)
Heterobimetallic Lewis acids M3(THF)n(BINOLate) 3Ln [M = Li, Na, K; Ln = lanthanide(III)] are exceptionally useful asymmetric catalysts that exhibit high levels of enantioselectivity across a wide range of reactions. Despi
An efficient and simple strategy toward the synthesis of highly functionalized compounds
Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi
, p. 978 - 995 (2021/08/06)
The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.
The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates
Rádai, Zita,Kiss, Nóra Zsuzsa,Czugler, Mátyás,Karaghiosoff, Konstantin,Keglevich, Gy?rgy
, p. 283 - 293 (2019/02/19)
The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy) (phenyl) methyl] phosphonate, C9H13O4P, dimet
Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
Rádai, Zita,Windt, Tímea,Nagy, Veronika,Füredi, András,Kiss, Nóra Zsuzsa,Ranelovi?, Ivan,Tóvári, József,Keglevich, Gy?rgy,Szakács, Gergely,Tóth, Szilárd
supporting information, p. 14028 - 14035 (2019/09/18)
We synthesized substituted benzaldehyde derived α-hydroxyphosphonates (αOHP), α-hydroxyphosphonic acids (αOHPA) and α-phosphinoyloxyphosphonates (αOPP) and characterized their cytotoxicity against a panel of cancer cell lines. A library containing 56 analogues was screened against Mes-Sa parental and Mes-Sa/Dx5 multidrug resistant uterine sarcoma cell lines, using a fluorescence-based cytotoxicity assay. The cytotoxicity screening revealed that dibenzyl-αOHPs and dimethyl-α-diphenyl-OPPs were the most active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure-activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line Mes-Sa/Dx5, suggesting these compounds may overcome P-glycoprotein mediated multidrug resistance by evading the drug transporter.
Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation
Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 2554 - 2558 (2019/04/30)
A promiscuous lipase-catalyzed carbon-phosphorus bond formation is presented. The developed enzymatic Pudovik-Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α-hyd
Phosphorylation of (1-aryl-1-hydroxymethyl)phosphonates
Rádai, Zita,Hodula, Viktória,Kiss, Nóra Zsuzsa,Kóti, János,Keglevich, Gy?rgy
, p. 153 - 154 (2019/04/25)
The reaction of dimethyl (1-aryl-1-hydroxymethyl)phosphonates with 1-chloro-3-phospholene 1-oxides, diphenylphosphinic chloride or diphenyl chloridophosphonate affords the corresponding (1-phosphoryloxymethyl)phosphonates. The products with two different
Rational synthesis of α-hydroxyphosphonic derivatives including dronic acids
Grün, Alajos,Rádai, Zita,S?regi-Nagy, Dávid Illés,Greiner, István,Keglevich, Gy?rgy
, p. 386 - 387 (2019/01/18)
New, green methods have been elaborated for the syntheses of α-hydroxyphosphonates and α-hydroxymethylenebisphosphonic derivatives (HMBPs, dronates). α-Hydroxyphosphonates were prepared via the Pudovik reaction, while the synthesis of HMBPs has been performed in the three-component reaction of carboxylic acids, phosphorus trichloride and phosphorus acid.
