72019-14-8Relevant academic research and scientific papers
Convenient and regioselective one-pot solvent-free synthesis of β-hydroxyphosphonates
Sardarian,Shahsavari-Fard
, p. 289 - 295 (2007)
A simple, efficient, regioselective, and solvent-free method has been developed for the synthesis of β-hydroxyphosphonates from epoxides and triethyl phosphite using ZnCl2 in high yields under mild conditions. Copyright Taylor & Francis Group, LLC.
A β - hydroxyalkanephosphonic ester derivatives
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Paragraph 0047-0051, (2017/08/31)
The invention discloses a preparation method of beta-hydroxyphosphonate derivatives. The preparation method comprises that an arylethene derivative, a phosphorus reagent and manganese acetate are dissolved in a solvent and the solution undergoes a reactio
Mn(OAc)3-mediated synthesis of β-hydroxyphosphonates from P(O)-H compounds and alkenes
Gao, Yuzhen,Wu, Ju,Xu, Jian,Zhang, Pengbo,Tang, Guo,Zhao, Yufen
, p. 51776 - 51779 (2014/12/10)
A new and general method for the synthesis of β-hydroxy phosphonates has been achieved through Mn(OAc)3-mediated radical oxidative phosphonation of alkenes with H-phosphonates and H-phosphine oxide. The starting materials of P(O)-H compounds and alkenes are stable and cheap. Mn(OAc)3 can be readily prepared from Mn(OAc)2 in the laboratory. This method can be easily adapted to large-scale preparations. This journal is
Synthesis of β-hydroxyphosphonates by iron-catalyzed oxidative addition of phosphonyl radicals to alkenes
Taniguchi, Tsuyoshi,Idota, Atsushi,Yokoyama, Shin'Ichi,Ishibashi, Hiroyuki
experimental part, p. 4768 - 4770 (2011/10/02)
Phosphorohydrazidates have been shown to work as radical precursors by iron-catalyzed aerobic oxidation to generate corresponding phosphonyl radicals. Generated radicals cause intermolecular addition to various alkenes in the presence of molecular oxygen
Nonenzymatic kinetic resolution of racemic β-hydroxyalkanephosphonates with a chiral copper catalyst
Moriyama, Atsushi,Matsumura, Shintaro,Kuriyama, Masami,Onomura, Osamu
experimental part, p. 810 - 824 (2010/11/04)
Kinetic resolution of β-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21.
Reformatsky reactions with SmI2 in catalytic amount
Orsini, Fulvia,Lucci, Elvira Maria
, p. 1909 - 1911 (2007/10/03)
A substoichiometric protocol for Reformatsky-type addition of α-haloesters, α-haloketones, α-halonitriles, and α-halophosphonates to carbonyl compounds has been developed. β-Hydroxyesters and β-hydroxynitriles were obtained in good to excellent yields.
A New Horner-Wadsworth-Emmons type coupling reaction between nonstabilized β-hydroxy phosphonates and aldehydes or ketones
Reichwein, John F.,Pagenkopf, Brian L.
, p. 1821 - 1824 (2007/10/03)
Treatment of nonstabilized β-hydroxy phosphonic acid mono methyl esters with diisopropyl carbodiimide at ambient temperature leads to clean stereospecific elimination. The phosphonic acid mono alkyl esters are accessible by the selective partial saponification of dimethyl or diethyl alkyl phosphonates with NaOH or MgBr2. Isolated yields over both hydrolysis and elimination steps average 55-75%.
A new entry to β-hydroxyphosphonates: The SmI2-mediated reaction of diethyl iodomethylphosphonate with carbonyl compounds
Orsini, Fulvia,Caselli, Alessandro
, p. 7255 - 7257 (2007/10/03)
In the presence of samarium iodide α-halophosphonates react with aliphatic carbonyl compounds (aldehydes and ketones) to afford β-hydroxyphosphonates in fairly good yields under neutral and mild conditions. Lower yields are obtained with aromatic carbonyl compounds.
Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
Zurawinski, Remigiusz,Nakamura, Kaoru,Drabowicz, Jozef,Kielbasinski, Piotr,Mikolajczyk, Marian
, p. 3139 - 3145 (2007/10/03)
A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%.
