title: Divergent, stereoselective access to heterocyclic α,α-quaternary- and β(2,3,3)-amino acid derivatives from a N-Pmp-protected Orn-derived β-lactam.
abstract: A 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(2,3,3)-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.
authors: Instituto de Química Médica (IQM-CSIC), Juan de la Cierva, 3, 28006 Madrid, Spain. rosario.gonzalezmuniz@iqm.csic.es.
authors: Diego
authors: D
authors: Núñez-Villanueva
authors: M Teresa
authors: MT
authors: García-López
authors: Mercedes
authors: M
authors: Martín-Martínez
authors: Rosario
authors: R
authors: González-Muñiz
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D006571:Heterocyclic Compounds / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D006571:Heterocyclic Compounds; D047090:beta-Lactams