Diastereoselective synthesis of (+/-)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA.
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.
Hanrahan
Jane R
JR
The Faculty of Pharmacy, University of Sydney, NSW, Australia. janeh@pharm.usyd.edu.au
Mewett
Kenneth N
KN
Chebib
Mary
M
Matos
Susana
S
Eliopoulos
Con T
CT
Crean
Colm
C
Kumar
Rohan J
RJ
Burden
Peter
P
Johnston
Graham A R
GA
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*
D010721:Phosphinic Acids; D005680:gamma-Aminobutyric Acid