A CONCISE SYNTHESIS OF PIPERAZINE-2-CARBOXYLIC ACIDS VIA BETA-LACTAM-DERIVED ALPHA-AMINO-ACID N-CARBOXY ANHYDRIDES

Authors
PALOMO C GANBOA I CUEVAS C BOSCHETTI C LINDEN A
Citation
C. Palomo et al., A CONCISE SYNTHESIS OF PIPERAZINE-2-CARBOXYLIC ACIDS VIA BETA-LACTAM-DERIVED ALPHA-AMINO-ACID N-CARBOXY ANHYDRIDES, Tetrahedron letters, 38(26), 1997, pp. 4643-4646
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
26
Year of publication
1997
Pages
4643 - 4646
Database
ISI
SICI code
0040-4039(1997)38:26<4643:ACSOPA>2.0.ZU;2-X
Abstract
A route to piperazine-fused 3-hydroxy beta-lactams was accomplished vi a [2+2] cycloaddition, of alkoxyketenes with imines derived from chira l alpha-amino aldehydes and chiral beta-aminoalcohols. The resulting b eta-lactams on exposure to 0.55M NaOCl and a catalytic amount of 2,2,6 ,6-tetramethylpiperidinyl-1-oxyl (TEMPO) afforded alpha-amino acid N-c arboxy anhydrides formally derived from piperazine-2-carboxylic acids. (C) 1997 Elsevier Science Ltd.