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

Organic & Biomolecular Chemistry Pub Date: 2006-06-01 DOI: 10.1039/B604002K

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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