Literature DB >> 24273443

Temporary Protection of H-Phosphinic Acids as a Synthetic Strategy.

Laëtitia Coudray1, Jean-Luc Montchamp.   

Abstract

H-Phosphinates obtained through various methodologies are protected directly via reaction with triethyl orthoacetate. The resulting products can be manipulated easily, and various synthetic reactions are presented. For example, application to the synthesis of aspartate transcarbamoylase (ATCase) or kynureninase inhibitors are illustrated. Other reactions, such as Sharpless' asymmetric dihydroxylation, or Grubbs' olefin cross-metathesis are also demonstrated.

Entities:  

Keywords:  Cross-Coupling; Metathesis; Palladium; Phosphorus; Synthesis

Year:  2009        PMID: 24273443      PMCID: PMC3836261          DOI: 10.1002/ejoc.200900694

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  35 in total

1.  Orthosilicate-mediated esterification of monosubstituted phosphinic acids

Authors: 
Journal:  Org Lett       Date:  2000-10-19       Impact factor: 6.005

2.  Synthesis of the nanomolar photoaffinity GABA(B) receptor ligand CGP 71872 reveals diversity in the tissue distribution of GABA(B) receptor forms.

Authors:  M Belley; R Sullivan; A Reeves; J Evans; G O'Neill; G Y Ng
Journal:  Bioorg Med Chem       Date:  1999-12       Impact factor: 3.641

Review 3.  Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis.

Authors:  Matthew D McReynolds; Joseph M Dougherty; Paul R Hanson
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

4.  Structure-based design and synthesis of phosphinate isosteres of phosphotyrosine for incorporation in Grb2-SH2 domain inhibitors. Part 2.

Authors:  C V Walker; G Caravatti; A A Denholm; J Egerton; A Faessler; P Furet; C García-Echeverría; B Gay; E Irving; K Jones; A Lambert; N J Press; J Woods
Journal:  Bioorg Med Chem Lett       Date:  2000-10-16       Impact factor: 2.823

5.  Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols.

Authors:  Karla Bravo-Altamirano; Jean-Luc Montchamp
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

6.  Diastereoselective ring-closing metathesis: synthesis of P-stereogenic phosphinates from prochiral phosphinic acid derivatives.

Authors:  Katherine S Dunne; Fabrice Bisaro; Barbara Odell; Jean-Marc Paris; Véronique Gouverneur
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

7.  NiCl2-catalyzed hydrophosphinylation.

Authors:  Patrice Ribière; Karla Bravo-Altamirano; Monika I Antczak; Jennifer D Hawkins; Jean-Luc Montchamp
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

8.  Palladium-catalyzed hydrophosphinylation of alkenes and alkynes.

Authors:  Sylvine Deprèle; Jean-Luc Montchamp
Journal:  J Am Chem Soc       Date:  2002-08-14       Impact factor: 15.419

9.  Submicromolar phosphinic inhibitors of Escherichia coli aspartate transcarbamoylase.

Authors:  Laëtitia Coudray; Evan R Kantrowitz; Jean-Luc Montchamp
Journal:  Bioorg Med Chem Lett       Date:  2008-12-06       Impact factor: 2.823

10.  Synthesis and pharmacological evaluation of novel gamma-aminobutyric acid type B (GABAB) receptor agonists as gastroesophageal reflux inhibitors.

Authors:  Christer Alstermark; Kosrat Amin; Sean R Dinn; Thomas Elebring; Ola Fjellström; Kevin Fitzpatrick; William B Geiss; Johan Gottfries; Peter R Guzzo; James P Harding; Anders Holmén; Mohit Kothare; Anders Lehmann; Jan P Mattsson; Karolina Nilsson; Gunnel Sundén; Marianne Swanson; Sverker von Unge; Alex M Woo; Michael J Wyle; Xiaozhang Zheng
Journal:  J Med Chem       Date:  2008-06-25       Impact factor: 7.446

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