Expedient preparation of all isomers of 2-Aminocyclobutanecarboxylic acid in enantiomerically pure form

Carlos Fernandes (1) , Elisabeth Pereira (1) , Sophie Faure (1) , David J Aitken (2)

1 SEESIB - Synthèse et étude de systèmes à intêret biologique
2 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

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 α-phenylethylamine derivative resolution and controlled cis-to-trans epimerization procedures, and proceeds with invariably high yields

Carlos Fernandes, Elisabeth Pereira, Sophie Faure, David J Aitken. Expedient preparation of all isomers of 2-Aminocyclobutanecarboxylic acid in enantiomerically pure form. Journal of Organic Chemistry, 2009, 74, pp.3217-3220. ⟨hal-00376781⟩