title: A refined synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids.
abstract: The synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids has been refined to improve both the efficiency and the simplicity. These improvements provide a shorter and easier access to the racemic cis-cyclobutane β-amino acid core. Derivatization of this material with a chiral non-racemic oxazolidin-2-one allows easy diastereoisomeric separation and presents the advantage of allowing the non-destructive cleavage of the chiral auxiliary either by hydrolysis or by ammonolysis, thus providing an efficacious access to N-protected derivatives of all four stereoisomers of Boc-2-aminocyclobutanecarboxylic acid.
authors.affiliation: Laboratoire de Synthèse Organique et Méthodologie, ICMMO (UMR 8182-CNRS), Université Paris-Sud 11, 15 rue Georges Clemenceau, 91405 Orsay Cedex, France.
authors.forename: Valérie
authors.initials: V
authors.lastname: Declerck
authors.forename: David J
authors.initials: DJ
authors.lastname: Aitken
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C542744:2-aminocyclobutanecarboxylic acid; D002264:Carboxylic Acids; D003503:Cyclobutanes; D023303:Oxazolidinones