Stereodivergent syntheses of the first bis(cyclobutane) β-dipeptides

Sandra Izquierdo, Marta Martín-Vilà, Albertina G. Moglioni, Vicenç Branchadell, Rosa M. Ortuo

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20 Citations (Scopus)

Abstract

The efficient synthesis of methyl 2-benzyloxycarbonylamino-(1S,2R)-cyclobutane-1-carboxylate starting from 2-methoxycarbonyl-(1R,2S)-cyclobutane-1-carboxylic acid is described. This β-amino acid derivative is antipodal with respect to the (1R,2S)-compound that was previously synthesized in our laboratory from the same chiral hemi ester. In turn, these enantiomeric β-amino acids have been self-condensed and coupled with one another to provide, respectively, enantiomeric and diastereomeric bis(cyclobutane) β-dipeptides. These products are the first reported β-amino acid oligomers containing two directly linked cyclobutane residues. © 2002 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2403-2405
JournalTetrahedron Asymmetry
Volume13
Issue number22
DOIs
Publication statusPublished - 13 Nov 2002

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