1067-71-6Relevant articles and documents
Addition of secondary amines to alkynephosphonates
Panarina,Dogadina,Ionin
, p. 1729 - 1737 (2003)
Addition of secondary amines to diethyl alkynephosphonates, catalyzed by Cu(I) salts, proceeds regio- and stereospecifically and yields diethyl (E)-2-diethylaminooalkenephosphonates. The E configuration was established by analysis of the vicinal coupling constants between the phosphorus and carbon nuclei in the 13C NMR spectra of the reaction products and model compounds: 3JPC is 6-10 Hz at the cis arrangement of the coupled nuclei and 16 Hz or higher at the trans arrangement. In all the diethyl diethylaminoalkenephosphonates obtained, 3JPC is about 5 Hz, suggesting cis addition.
A new synthesis of β-keto phosphonate from aryl epoxysulfones and dialkyl hydrogen phosphite
Koh, Young Joo,Oh, Dong Yung
, p. 2147 - 2148 (1993)
Reaction of α-subtituted arylsulfonyl epoxide with diethyl phosphite sodium salt gave β-keto phosphonate in good yield.
Making mixtures to solve structures: structural elucidation via combinatorial synthesis
Lengkeek, Nigel A.,Greenwood, Paul F.,Nguyen, Blake,Koutsantonis, George A.,Piggott, Matthew J.
, p. 141 - 150 (2010)
A domino Horner-Wadsworth-Emmons olefination strategy has been used to prepare homologous series of (polyen)ones, and through combinatorial elaboration, corresponding families of highly branched hydrocarbons. Gas chromatography-mass spectrometry of the mixtures has enabled the rapid and unambiguous identification of several highly branched alkanes of geochemical importance. This is the first example of the use of combinatorial synthesis for the elucidation of structural connectivity.
An expedient synthesis of diethyl diazomethylphosphonate
Kosobokov, Mikhail D.,Titanyuk, Igor D.,Beletskaya, Irina P.
, p. 142 - 143 (2011)
A simple three-step preparation of diethyl diazomethylphosphonate was performed from chloroacetone and triethyl phosphite in total yield 70%.
Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates
Fesenko, Anastasia A.,Cheshkov, Dmitrii A.,Shutalev, Anatoly D.
, p. 51 - 53 (2008)
The reaction of sodium enolate of diethyl (2-oxoprop-1-yl)phosphonate with N-(1-tosylprop-1-yl)thiourea results in the stereoselective formation of diethyl (4R*,5R*,6R*)-6-ethyl-4-hydroxy-4-methyl-2-thioxohexahydropyrimidine-5-phosphonate, which is transformed into diethyl 4-ethyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-phosphonate and diethyl (4R*,5S*,6R*)-4-ethyl-6-methyl-2-thioxohexahydropyrimidine-5-phosphonate by acid-catalysed dehydration and stereoselective reduction with NaBH4-CF3COOH, respectively.
REGIOCONTROLLED METALATION OF DIETYHL β-DIALKYLAMINOVINYLPHOSPHONATES: A NEW SYNTHESIS OF SUBSTITUTED β-KETOPHOSPHNATES
Boeckman, Robert K.,Walters, Michael A.,Koyano, Hiroshi
, p. 4787 - 4790 (1989)
The metalation of diethyl β-dialkylaminovinylphosphonates (vinylogous phosphoramides (VPA)) and their reaction with a variety of electrophiles is described.Upon mild hydrolysis these derivatives provide good yields of β-ketophosphonates.
A new and facile synthetic route to 1-alkyl-2-oxopropylphosphonates: 1 alkylation with subsequent ozonolysis of 2-methyl allylic phosphonates
Gil, Jun Mo,Park, Kwang Young,Hah, Jung Hwan,Oh, Dong Young
, p. 3601 - 3607 (1998)
Alkylation of the 2-methyl allylic phosphonates is performed by treatment with n-BuLi, followed by addition of alkyl halides. The 1-alkyl-2- oxopropylphosphonates are obtained by the ozonolysis of the corresponding allylic phosphonates.
Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
Zurawinski, Remigiusz,Nakamura, Kaoru,Drabowicz, Jozef,Kielbasinski, Piotr,Mikolajczyk, Marian
, p. 3139 - 3145 (2001)
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%.
Highly stereoselective synthesis of cyclopropylphosphonates catalyzed by chiral Ru(II)-pheox complex
Chanthamath, Soda,Ozaki, Seiya,Shibatomi, Kazutaka,Iwasa, Seiji
, p. 3012 - 3015 (2014)
Ru(II)-Pheox-catalyzed asymmetric cyclopropanation of diethyl diazomethylphosphonate with alkenes, including α,β-unsaturated carbonyl compounds, afforded the corresponding optically active cyclopropylphosphonates in high yields and with excellent diastereoselectivity (up to 99:1) and enantioselectivity (up to 99% ee).
Reactivity of [60]Fullerene with primary nitro compounds: Addition or catalysed condensation to isoxazolo[60]fullerenes
Biagiotti, Giacomo,Cicchi, Stefano,De Sarlo, Francesco,Machetti, Fabrizio
, p. 7906 - 7915 (2014)
The catalysed condensation of [60]fullerene with ethyl nitroacetate (1b) or analogous activated nitro derivatives to afford isoxazolino[60]fullerenes has been achieved in both homogeneous and heterogeneous conditions. This direct synthetic approach is more convenient than previous methods. Model reactions with electron-poor dipolarophiles led to either condensation to isoxazolines or to conjugate addition products, depending on the nitro compound and catalyst. The former product was favoured by the use of CuII in the catalytic system. Conversely, [60]fullerene underwent catalytic condensation, even in the absence of copper(II) salts, only with activated nitro compounds and addition only with nitroalkanes in excess base. Note, the formal conjugated fullerene addition product was obtained in isomeric form, as previously reported. A possible explanation is presented for this contrasting behaviour.
