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Quaternary α,α-2-oxoazepane α-amino acids: Synthesis from ornithine-derived β-lactams and incorporation into model dipeptides

AuthorsNúñez Villanueva, Digo; Bonache de Marcos, María Ángeles ; Infantes, L. ; García-López, M. Teresa ; Martín-Martínez, Mercedes ; González-Muñiz, Rosario
Issue Date2011
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 76: 6592- 6603 (2011)
AbstractTo explore further the chemistry of amino acid-derived β-lactams, their conversion to α,α-heterocyclic quaternary amino acid derivatives is investigated. The latter derivatives, containing 2-oxoazepane as the α,α-substituent, are synthesized by a simple Pd-C-catalyzed hydrogenolysis of Orn(Z)-derived 2-azetidinones. The rearrangement from four- to seven-membered lactam ring is driven by the key intramolecular opening of the 1-Boc-β-lactam, initiated by 7-exotrig ring closure from the NH2 of the Orn side chain. The synthetic route is applied to the stereoselective preparation of enantiomerically pure 4-amino-3-methyl-2-oxoazepane-4-carboxylate derivatives, for which the structure and configuration is confirmed by X-ray diffraction. Molecular modeling and NMR experiments indicate that these quaternary amino acids are able to drive the adoption of β-turn secondary structures when incorporated in model dipeptide derivatives.
Identifiersdoi: 10.1021/jo200894d
issn: 0022-3263
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