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Literature DB >> 17352490

Alkylation of H-phosphinate esters under basic conditions.

Isabelle Abrunhosa-Thomas¹, Claire E Sellers, Jean-Luc Montchamp.

Abstract

An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17352490 PMCID： PMC2525801 DOI： 10.1021/jo062436o

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

26 in total

Review 1. Ligands for expression cloning and isolation of GABA(B) receptors.

Authors: Wolfgang Froestl; Bernhard Bettler; Helmut Bittiger; Jakob Heid; Klemens Kaupmann; Stuart J Mickel; Dietrich Strub
Journal: Farmaco Date: 2003-03

2. Orthosilicate-mediated esterification of monosubstituted phosphinic acids

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

3. (Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE.

Authors: D S Karanewsky; M C Badia; D W Cushman; J M DeForrest; T Dejneka; M J Loots; M G Perri; E W Petrillo; J R Powell
Journal: J Med Chem Date: 1988-01 Impact factor: 7.446

4. Investigations on New Strategies for the Facile Synthesis of Polyfunctionalized Phosphinates: Phosphinopeptide Analogues of Glutathionylspermidine.

Authors: Shoujun Chen; James K. Coward
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

5. 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

6. 3-Deoxy-D-myo-inositol 1-phosphate, 1-phosphonate, and ether lipid analogues as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth.

Authors: L Qiao; F Nan; M Kunkel; A Gallegos; G Powis; A P Kozikowski
Journal: J Med Chem Date: 1998-08-27 Impact factor: 7.446

7. Studies on phosphonic acid antibiotics. IV. Synthesis and antibacterial activity of analogs of 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid (FR-900098).

Authors: K Hemmi; H Takeno; M Hashimoto; T Kamiya
Journal: Chem Pharm Bull (Tokyo) Date: 1982-01 Impact factor: 1.645

Review 8. Herbicidal inhibitors of amino acid biosynthesis and herbicide-tolerant crops.

Authors: S Tan; R Evans; B Singh
Journal: Amino Acids Date: 2006-03-20 Impact factor: 3.520

9. Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated alpha-linked acidic dipeptidase.

Authors: P F Jackson; D C Cole; B S Slusher; S L Stetz; L E Ross; B A Donzanti; D A Trainor
Journal: J Med Chem Date: 1996-01-19 Impact factor: 7.446

10. 1,1-Bisphosphonate squalene synthase inhibitors: interplay between the isoprenoid subunit and the diphosphate surrogate.

Authors: D R Magnin; S A Biller; J K Dickson; J V Logan; R M Lawrence; Y Chen; R B Sulsky; C P Ciosek; T W Harrity; K G Jolibois
Journal: J Med Chem Date: 1995-07-07 Impact factor: 7.446

6 in total

Alkylation of H-phosphinate esters under basic conditions.

Review 1. Ligands for expression cloning and isolation of GABA(B) receptors.

2. Orthosilicate-mediated esterification of monosubstituted phosphinic acids

3. (Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE.

4. Investigations on New Strategies for the Facile Synthesis of Polyfunctionalized Phosphinates: Phosphinopeptide Analogues of Glutathionylspermidine.

5. NiCl2-catalyzed hydrophosphinylation.

6. 3-Deoxy-D-myo-inositol 1-phosphate, 1-phosphonate, and ether lipid analogues as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth.

7. Studies on phosphonic acid antibiotics. IV. Synthesis and antibacterial activity of analogs of 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid (FR-900098).

Review 8. Herbicidal inhibitors of amino acid biosynthesis and herbicide-tolerant crops.

9. Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated alpha-linked acidic dipeptidase.

10. 1,1-Bisphosphonate squalene synthase inhibitors: interplay between the isoprenoid subunit and the diphosphate surrogate.

1. Synthesis and Reactivity Studies of α,α-Difluoromethylphosphinates.

2. Borane Complexes of the H(3)PO(2) P(III) Tautomer: Useful Phosphinate Equivalents.

3. Heteroatom analogues of hydrocodone: synthesis and biological activity.

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

5. Benz-yl(meth-yl)phosphinic acid.

Review 6. Phosphinate-containing heterocycles: A mini-review.