Expedient preparation of all isomers of 2-aminocyclobutanecarboxylic acid in enantiomerically pure form.
A short, convenient, gram scale protocol has been established to allow facile access to all four stereoisomers of 2-aminocyclobutanecarboxylic acid, each in enantiomerically pure form (ee >99%). Starting from the readily available cis racemate, the procedure combines efficient alpha-phenylethylamine derivative resolution and controlled cis-to-trans epimerization procedures, and proceeds with invariably high yields.
Fernandes
Carlos
C
Laboratoire SEESIB (UMR 6504-CNRS), Département de Chimie, Université Blaise Pascal-Clermont-Ferrand 2, 24 Avenue des Landais, 63177 Aubière cedex, France.
Pereira
Elisabeth
E
Faure
Sophie
S
Aitken
David J
DJ
D000577:Amides / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C542744:2-aminocyclobutanecarboxylic acid; D000577:Amides; D002264:Carboxylic Acids; D003503:Cyclobutanes; D010627:Phenethylamines; C033198:1-phenethylamine