Issue 13, 2006
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective synthesis of (±)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA

Jane R. Hanrahan,*a   Kenneth N. Mewett,b   Mary Chebib,a   Susana Matos,a   Con T. Eliopoulos,b   Colm Crean,a   Rohan J. Kumar,a   Peter Burdenb  and  Graham A. R. Johnstonb  

* Corresponding authors

a The Faculty of Pharmacy, University of Sydney, NSW, Australia
E-mail: janeh@pharm.usyd.edu.au
Fax: +61 2 9351 4391
Tel: +61 2 9351 2078

b The Adrien Albert Laboratory of Medicinal Chemistry, Department of Pharmacology, The University of Sydney, NSW, Australia
E-mail: grahamj@mail.usyd.edu.au
Fax: +61 2 9351 2891
Tel: +61 2 9351 6117

Abstract

A divergent synthesis of both diastereoisomers of (±)-(3-aminocyclopentane)alkylphosphinic acid is described. Both diastereoisomers are obtained in 5 steps from the key (±)-(3-hydroxycyclopent-1-ene)alkylphosphinate esters which are prepared via a palladium catalysed C–P bond forming reaction.

Graphical abstract: Diastereoselective synthesis of (±)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA

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Article information

DOI
https://doi.org/10.1039/B604002K
Article type
Paper
Submitted
17 Mar 2006
Accepted
22 May 2006
First published
01 Jun 2006

Org. Biomol. Chem., 2006,4, 2642-2649

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Diastereoselective synthesis of (±)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA

J. R. Hanrahan, K. N. Mewett, M. Chebib, S. Matos, C. T. Eliopoulos, C. Crean, R. J. Kumar, P. Burden and G. A. R. Johnston, Org. Biomol. Chem., 2006, 4, 2642 DOI: 10.1039/B604002K

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