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

Org Biomol Chem. 2006 Jul 7;4(13):2642-9. doi: 10.1039/b604002k. Epub 2006 Jun 1.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Phosphinic Acids / chemical synthesis*
  • Phosphinic Acids / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • gamma-Aminobutyric Acid / analogs & derivatives*


  • Phosphinic Acids
  • gamma-Aminobutyric Acid