Issue 18, 2015

Divergent, stereoselective access to heterocyclic α,α-quaternary- and β2,3,3-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-β2,3,3-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.

Graphical abstract: Divergent, stereoselective access to heterocyclic α,α-quaternary- and β2,3,3-amino acid derivatives from a N-Pmp-protected Orn-derived β-lactam

Supplementary files

Article information

Article type
Paper
Submitted
03 Mar 2015
Accepted
25 Mar 2015
First published
26 Mar 2015

Org. Biomol. Chem., 2015,13, 5195-5201

Author version available

Divergent, stereoselective access to heterocyclic α,α-quaternary- and β2,3,3-amino acid derivatives from a N-Pmp-protected Orn-derived β-lactam

D. Núñez-Villanueva, M. T. García-López, M. Martín-Martínez and R. González-Muñiz, Org. Biomol. Chem., 2015, 13, 5195 DOI: 10.1039/C5OB00429B

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