title: Diastereoselective synthesis of (+/-)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA.
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.
authors.affiliation: The Faculty of Pharmacy, University of Sydney, NSW, Australia. janeh@pharm.usyd.edu.au
authors.forename: Jane R
authors.initials: JR
authors.lastname: Hanrahan
authors.forename: Kenneth N
authors.initials: KN
authors.lastname: Mewett
authors.forename: Mary
authors.initials: M
authors.lastname: Chebib
authors.forename: Susana
authors.initials: S
authors.lastname: Matos
authors.forename: Con T
authors.initials: CT
authors.lastname: Eliopoulos
authors.forename: Colm
authors.initials: C
authors.lastname: Crean
authors.forename: Rohan J
authors.initials: RJ
authors.lastname: Kumar
authors.forename: Peter
authors.initials: P
authors.lastname: Burden
authors.forename: Graham A R
authors.initials: GA
authors.lastname: Johnston
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives*
chemical_list: D010721:Phosphinic Acids; D005680:gamma-Aminobutyric Acid