2024-03-28T14:05:51Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1177032016-02-18T03:17:00Zcom_10261_81com_10261_5col_10261_334
00925njm 22002777a 4500
dc
Núñez-Villanueva, D.
author
García López, María Teresa
author
Martín Martínez, María Mercedes
author
González-Muñiz, Rosario
author
2015
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<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.
Organic and Biomolecular Chemistry 13: 5195-5201 (2015)
http://hdl.handle.net/10261/117703
10.1039/c5ob00429b
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