2942-54-3Relevant articles and documents
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.
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.
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
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
Nicotinium dichromate (= 3-carboxypyridinium dichromate; NDC) as an efficient reagent for the oxidative deamination of amines and aminophosphonates
Sobhani, Sara,Aryanejad, Sima,Maleki, Mahdi Faal
experimental part, p. 613 - 617 (2012/05/20)
A new method for the efficient synthesis of aldehydes, ketones, and oxophosphonates from various types of amines (primary and secondary) and aminophosphonates via oxidative deamination by nicotinium dichromate (= 3-carboxypyridinium dichromate; NDC) is described.
