Literature DB >> 20871799

An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives.

Mario Ordóñez1, Haydée Rojas-Cabrera, Carlos Cativiela.   

Abstract

An overview of all methodologies published during the last few years focused to the stereoselective (diastereoselective or enantioselective) synthesis of α-aminophosphonic acids and derivatives is reported. The procedures have been classified according a retrosynthetic strategy and taking into account the formation of each one of the bonds connected to the chiral centre.

Entities:  

Year:  2009        PMID： 20871799      PMCID： PMC2943650          DOI： 10.1016/j.tet.2008.09.083

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  102 in total

1.  2H-Azirine 3-phosphonates: a new class of chiral iminodienophiles. Asymmetric synthesis of quaternary piperidine phosphonates.

Authors:  Franklin A Davis; Yongzhong Wu; Hongxing Yan; Kavirayani R Prasad; William McCoull
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

2.  [Cloning and identification of cellulase genes from uncultured microorganisms in pulp sediments from paper mill effluent].

Authors:  Yue-Qiang Xu; Cheng-Jie Duan; Quan-Neng Zhou; Ji-Liang Tang; Jia-Xun Feng
Journal:  Wei Sheng Wu Xue Bao       Date:  2006-10

3.  Phosphonopeptides as antibacterial agents: rationale, chemistry, and structure-activity relationships.

Authors:  F R Atherton; M J Hall; C H Hassall; R W Lambert; P S Ringrose
Journal:  Antimicrob Agents Chemother       Date:  1979-05       Impact factor: 5.191

4.  Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action.

Authors:  S De Lombaert; L Blanchard; L B Stamford; J Tan; E M Wallace; Y Satoh; J Fitt; D Hoyer; D Simonsbergen; J Moliterni; N Marcopoulos; P Savage; M Chou; A J Trapani; A Y Jeng
Journal:  J Med Chem       Date:  2000-02-10       Impact factor: 7.446

5.  alpha-Biphenylsulfonylamino 2-methylpropyl phosphonates: enantioselective synthesis and selective inhibition of MMPs.

Authors:  Alessandro Biasone; Paolo Tortorella; Cristina Campestre; Mariangela Agamennone; Serena Preziuso; Marika Chiappini; Elisa Nuti; Paolo Carelli; Armando Rossello; Fernando Mazza; Carlo Gallina
Journal:  Bioorg Med Chem       Date:  2006-10-25       Impact factor: 3.641

6.  N-phosphonoalkyl-5-aminomethylquinoxaline-2,3-diones: in vivo active AMPA and NMDA(glycine) antagonists.

Authors:  Y P Auberson; P Acklin; S Bischoff; R Moretti; S Ofner; M Schmutz; S J Veenstra
Journal:  Bioorg Med Chem Lett       Date:  1999-01-18       Impact factor: 2.823

7.  Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase.

Authors:  J Bird; R C De Mello; G P Harper; D J Hunter; E H Karran; R E Markwell; A J Miles-Williams; S S Rahman; R W Ward
Journal:  J Med Chem       Date:  1994-01-07       Impact factor: 7.446

8.  Asymmetric synthesis of cyclic alpha-amino phosphonates using masked oxo sulfinimines (N-sulfinyl imines).

Authors:  Franklin A Davis; Seung H Lee; He Xu
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

9.  A new enzyme model for enantioselective esterases based on molecularly imprinted polymers.

Authors:  Marco Emgenbroich; Günter Wulff
Journal:  Chemistry       Date:  2003-09-05       Impact factor: 5.236

10.  Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and delta-amino beta-ketophosphonates.

Authors:  Franklin A Davis; Yongzhong Wu; He Xu; Junyi Zhang
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005
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  17 in total

1.  NCAD, a database integrating the intrinsic conformational preferences of non-coded amino acids.

Authors:  Guillem Revilla-López; Juan Torras; David Curcó; Jordi Casanovas; M Isabel Calaza; David Zanuy; Ana I Jiménez; Carlos Cativiela; Ruth Nussinov; Piotr Grodzinski; Carlos Alemán
Journal:  J Phys Chem B       Date:  2010-06-03       Impact factor: 2.991

2.  Aqua-soluble DDQ reduces the levels of Drp1 and Aβ and inhibits abnormal interactions between Aβ and Drp1 and protects Alzheimer's disease neurons from Aβ- and Drp1-induced mitochondrial and synaptic toxicities.

Authors:  Chandra Sekhar Kuruva; Maria Manczak; Xiangling Yin; Gilbert Ogunmokun; Arubala P Reddy; P Hemachandra Reddy
Journal:  Hum Mol Genet       Date:  2017-09-01       Impact factor: 6.150

3.  Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Authors:  Deepankar Das; Daniel Seidel
Journal:  Org Lett       Date:  2013-08-19       Impact factor: 6.005

4.  Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides.

Authors:  Gajendrasingh K Ingle; Yuxue Liang; Michael G Mormino; Guilong Li; Frank R Fronczek; Jon C Antilla
Journal:  Org Lett       Date:  2011-03-17       Impact factor: 6.005

5.  Novel α-Aminophosphonates and α-Aminophosphonic Acids: Synthesis, Molecular Docking and Evaluation of Antifungal Activity against Scedosporium Species.

Authors:  Anthonny Cordero-Díaz; Efren Robledo-Leal; Eugenio Hernández-Fernández; Emanuel Hernández-Núñez; Mariana Elizondo-Zertuche; Susana T López-Cortina
Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927

6.  Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of α-hydroxyphosphonates induced by deoxyfluorinating reagents.

Authors:  Patrycja Kaczmarek; Magdalena Rapp; Henryk Koroniak
Journal:  RSC Adv       Date:  2018-07-06       Impact factor: 4.036

7.  Squaramide-catalyzed enantioselective Michael addition of diphenyl phosphite to nitroalkenes.

Authors:  Ye Zhu; Jeremiah P Malerich; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

8.  Fungal platform for direct chiral phosphonic building blocks production. Closer look on conversion pathway.

Authors:  Ewa Żymańczyk-Duda; Małgorzata Brzezińska-Rodak; Kinga Kozyra; Magdalena Klimek-Ochab
Journal:  Appl Biochem Biotechnol       Date:  2014-11-16       Impact factor: 2.926

9.  Low cytotoxicity and clastogenicity of some polymeric aminophosphonate derivatives.

Authors:  Anton Kril; Margarita Topashka-Ancheva; Any Georgieva; Ivan Iliev; Tsvetelina Gerasimova; Ivanka Kraicheva; Ivelina Tsacheva; Anita Bogomilova; Elitsa Vodenicharova; Kolio Troev
Journal:  Biotechnol Biotechnol Equip       Date:  2014-01-02       Impact factor: 1.632

10.  Highly Diastereoselective Construction of Carbon- Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates.

Authors:  Magdalena Rapp; Klaudia Margas-Musielak; Patrycja Kaczmarek; Agnieszka Witkowska; Tomasz Cytlak; Tomasz Siodła; Henryk Koroniak
Journal:  Front Chem       Date:  2021-06-02       Impact factor: 5.221
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