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Título

Divergent, stereoselective access to heterocyclic α,α-quaternary- and β<sup>2,3,3</sup>-amino acid derivatives from a N-Pmp-protected Orn-derived β-lactam

AutorNúñez-Villanueva, D. ; García López, María Teresa; Martín Martínez, María Mercedes; González-Muñiz, Rosario
Fecha de publicación2015
EditorRoyal Society of Chemistry (Great Britain)
CitaciónOrganic and Biomolecular Chemistry 13: 5195-5201 (2015)
ResumenA suitably protected Orn-derived (3S,4S)-β-lactam was used as common intermediate in the synthesis of conformationally constrained (3S,4S)-2-oxoazepane α,α- and (2S,3S)-2-oxopiperidine-β<sup>2,3,3</sup>-amino acid derivatives. Compared to alternative procedures using an N-p-methoxybenzyl group at the 2-azetidinone, the incorporation of a p-methoxyphenyl moiety is crucial for the excellent stereochemical outcomes in the preparation of these heterocyclic amino acids. Chemoselective 7- or 6-exo-trig cyclization was achieved through alternative sequences of Pmp-deprotection/Boc-activation, followed by inter- and intramolecular β-lactam ring opening, respectively.
URIhttp://hdl.handle.net/10261/117703
DOI10.1039/c5ob00429b
Identificadoresdoi: 10.1039/c5ob00429b
issn: 1477-0520
e-issn: 1477-0539
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