2942-54-3Relevant academic research and scientific papers
A convenient and mild protocol for preparation of α – trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide
Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
, (2021/10/05)
A convenient and mild protocol was developed for the trimethylsilylation of α-hydroxyphosphonates using hexamethyldisilazane as the silylating agent in the presence of sulfamic acid (SA) as a heterogeneous solid acid catalyst in dichloromethane as the rea
Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles
Jaiswal, Manish K.,Singh, Ravi P.,Singh, Sanjay
supporting information, p. 7861 - 7866 (2021/09/28)
A simple strategy for yielding chiral tertiary α-hydroxy phosphonates that integrates two highly biologically relevant scaffolds namely 3-alkylidene-2-oxindoles and phosphonates has been described. The hydrogen bonding ability of the bifunctional thiourea catalyst allows simultaneous dual activation of a vinylogous oxindole nucleophile and an acylphosphonate electrophile, affording hydroxyphosphonato-3-alkylidene-2-oxindoles as aldol adducts in high yields (up to 92%) with excellent stereocontrol (up to 99% ee).
Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane
Kupwade, Ravindra V.,Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
, p. 50 - 58 (2021/02/26)
Dess-Martin periodinane has been demonstrated for the first time to be an efficient reagent in metal - free oxidation of α-hydroxyphosphonates to α-ketophosphonates under ambient conditions. Acquiescent reaction conditions and a simple isolation procedure
Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates
Li, Yong-Hong,Wang, Chun-Hai,Gao, Su-Qian,Qi, Feng-Ming,Yang, Shang-Dong
supporting information, p. 11888 - 11891 (2019/10/11)
A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C-P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3-P and Csp3-N bonds without the requirement for oxidants and bases.
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.
Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates
Kayal, Satavisha,Mukherjee, Santanu
supporting information, p. 5508 - 5511 (2015/11/18)
A cascade aldol-cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction
Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
Lian, Zhong,Yin, Hongfei,Friis, Stig D.,Skrydstrup, Troels
supporting information, p. 7831 - 7834 (2015/05/13)
The first transition-metal catalysed carbonylation with a phosphorus nucleophile is presented. This transformation provides efficient and mild access to aroylphosphonates under mild conditions, thus ensuring a broad substrate scope. The utility of aroylph
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.
Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst
Jang, Ki Po,Hutson, Gerri E.,Johnston, Ryne C.,McCusker, Elizabeth O.,Cheong, Paul H.-Y.,Scheidt, Karl A.
supporting information, p. 76 - 79 (2014/01/23)
A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enanti
Benzoylphosphonate-based photoactive phosphopeptide mimetics for modulation of protein tyrosine phosphatases and highly specific labeling of SH2 domains
Horatscheck, André,Wagner, Stefan,Ortwein, Jutta,Kim, Boo Geun,Lisurek, Michael,Beligny, Samuel,Schütz, Anja,Rademann, J?rg
, p. 9441 - 9447 (2012/10/29)
A light switch for phosphotyrosine- recognizing proteins: Irradiation of the bioisosteric benzoylphosphonate suffices to "turn off" the activity of target proteins and to label them covalently (see scheme). Photoactive bioisosters may find applications in functional cell biology, bioanalytics, and proteome research.
