22950-57-8Relevant academic research and scientific papers
Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates
Sun, Jun,He, Fangcheng,Wang, Zhongyao,Pan, Dingwu,Zheng, Pengcheng,Mou, Chengli,Jin, Zhichao,Chi, Yonggui Robin
supporting information, p. 6040 - 6043 (2018/06/18)
A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.
Synthesis of acylphosphonates by a palladium-catalyzed phosphonocarbonylation reaction of aryl iodides with phosphites
Masuda, Yusuke,Ishida, Naoki,Murakami, Masahiro
supporting information, p. 321 - 324 (2015/02/05)
Acylphosphonates are conveniently synthesized from aryl iodides by a palladium-catalyzed reaction with dialkyl phosphites under an atmospheric pressure of carbon monoxide. The reaction demonstrates the first example of the use of phosphorus nucleophiles in related metal-catalyzed carbonylation reactions.
Rhodium-catalyzed enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates: ligand- and substituent-controlled C-P or C-H bond cleavage
Masuda, Kengo,Sakiyama, Norifumi,Tanaka, Rie,Noguchi, Keiichi,Tanaka, Ken
supporting information; experimental part, p. 6918 - 6921 (2011/06/21)
It has been established that a cationic rhodium(I)/(R)-H8-BINAP or (R)-Segphos complex catalyzes two modes of enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates via C-P or C-H bond cleavage. The ligands of the Rh(I) comp
Asymmetric hydrogenation of α-keto phosphonates with chiral palladium catalysts
Goulioukina, Nataliya S.,Bondarenko, Grigorii N.,Bogdanov, Alexei V.,Gavrilov, Konstantin N.,Beletskaya, Irina P.
experimental part, p. 510 - 515 (2009/07/19)
Under atmospheric hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and (R)-MeO-BIPHEP in 2,2,2-trifluoroethanol promoted the asymmetric hydrogenation of diisopropyl α-keto phosphonates 1 to afford the corresponding α-hydroxy phospho
Reactions of acyl tributylphosphonium chlorides and dialkyl acylphosphonates with Grignard and organolithium reagents
Maeda, Hatsuo,Takahashi, Kenji,Ohmori, Hidenobu
, p. 12233 - 12242 (2007/10/03)
Ketones and esters (4) were effectively prepared by reaction of Grignard reagents with acyl tributylphosphonium chlorides (2), diethyl acylphosphonates (5), or diisopropyl acylphosphonate (6) derived from acid chlorides and chloroformates (1). Although by the method with 2, 4 is prepared in one-pot operation from 1 and generally in a higher yield, the method with 5 or 6 proved to compensate for the synthesis of 4 with 2 in some respects. The reactivities of 2, 5, and 6 as electrophiles were also evaluated by comparing their reduction potential with those of acid chlorides.
Asymmetric Synthesis of Chiral, Nonracemic Dialkyl α-Hydroxyarylmethyl- and α-, β- and γ-Hydroxyalkylphosphonates from Keto Phosphonates
Meier, Chris,Laux, Wolfgang H. G.,Bats, Jan W.
, p. 1963 - 1980 (2007/10/03)
The enantioselective synthesis of α-hydroxyarylmethylphosphonates 2a-p by the oxazaborolidine-catalyzed reduction of α-keto phosphonates 1a-p using different boranes 4a-c was studied in detail.Moderate to good enantioselectivities are found (up to 80perce
Studies on organophosphorus compounds; LXXV: A facile synthesis of 1-(hydroxyamino)alkyl(or aryl)phosphonic acids
Yuan,Chen,Zhou,Maier
, p. 955 - 957 (2007/10/02)
Reduction of dialkyl 1-(hydroxyimino)alkyl(aryl)phosphonate 1 with borane-pyridine complex proceeds smoothly to give dialkyl 1-(hydroxyamino)alkyl(or aryl)phosphonate 2 which is then easily converted into the corresponding hydroxyaminophosphonic acid 3 by
THE REACTION OF BENZOYLPHOSPHONIC ACID WITH THIONYL CHLORIDE. THE FORMATION OF BENZOYLPHOSPHONIC DICHLORIDE AND P,P'-DIBENZOYLPYROPHOSPHONIC DICHLORIDE
Bentolila, Alfonso,Katzhendler, Jehoshua,Breuer, Eli
, p. 109 - 112 (2007/10/02)
The reaction of benzoylphosphonic acid (3) with thionyl chloride leads to the formation of benzoylphosphonic dichloride (5) and P,P'-dibenzoylpyrophosphonic dichloride (6).These products were identified by (31)P nmr spectra and through their products of a
Acylphosphonates: P-C Bond Cleavage of Dialkyl Acylphosphonates by Means of Amines. Substituent and Solvent Effects for Acylation of Amines
Sekine, Mitsuo,Satoh, Masaki,Yamagata, Hikaru,Hata, Tsujiaki
, p. 4162 - 4167 (2007/10/02)
Studies on the benzoylation of amines of dialkyl benzoylphosphonates (1A-F) were described in detail. Stoichiometric reactions of diethyl benzoylphosphonate (1B) with a variety of amines (2a-i) gave amides as the main products along with diethyl phosphonate (4B) and α-(phosphoryloxy)benzyl phosphonate (5B). The yields of amides increased with the ratio of 1B/2a-i. The use of hindered dialkyl benzoylphosphonates resulted in high yields of amides while the reaction rates decreased markedly. The benzoylations of n-propylamine (2d) with 1B in various solvents having dielectric constants of 1.9-36.7 were conducted. The yields of N-n-propylbenzamide (3d) and 5B were surprisingly almost constant. However, the reaction rates varied as follows. In nonpolar solvents such as n-hexane and cyclohexane benzoylation was remarkably rapid while the benzoylation in methylene chloride was much slower than that in other solvents used. Compound 1B underwent smooth reaction with aliphatic amines but did not react with aromatic amines under the same conditions. Selective N-benzoylation of the bifunctional amine, ethanolamine, was achieved by means of diisopropyl benzoylphosphonate (1C) in tetrahydrofuran. The use of the hindered dialkyl benzoylphosphonate 1C resulted in poorer yields of amides in the case of the reaction with a hindered amine such as diethylamine, but higher yields of amides in the case of primary amines. Addition of triethylamine and 4-(dimethylamino)pyridine (DMAP) slightly accelerated the benzoylation, but yields of amides were similar to those in the absence of the catalysts. Optimum conditions for high yields of amides were proposed for the practical use of dialkyl benzoylphosphonates as the acylating agents in the present reaction.
