GENERATION OF THREONINE AND AZATHREONINE N-CARBOXY ANHYDRIDES FROM ALPHA-HYDROXY BETA-LACTAMS PROMOTED BY 2,2,6,6-TETRAMETHYLPIPERIDINYL-1-OXYL (TEMPO) IN COMBINATION WITH SODIUM-HYPOCHLORITE

Authors
PALOMO C AIZPURUA JM CUEVAS C URCHEGUI R LINDEN A
Citation
C. Palomo et al., GENERATION OF THREONINE AND AZATHREONINE N-CARBOXY ANHYDRIDES FROM ALPHA-HYDROXY BETA-LACTAMS PROMOTED BY 2,2,6,6-TETRAMETHYLPIPERIDINYL-1-OXYL (TEMPO) IN COMBINATION WITH SODIUM-HYPOCHLORITE, Journal of organic chemistry, 61(13), 1996, pp. 4400-4404
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
13
Year of publication
1996
Pages
4400 - 4404
Database
ISI
SICI code
0022-3263(1996)61:13<4400:GOTAAN>2.0.ZU;2-U
Abstract
A versatile one-pot oxidation-Baeyer-Villiger reaction sequence applie d to alpha-hydroxy beta-lactams and promoted by 2,2,6,6-tetramethylpip eridinyl-1-oxyl (TEMPO) leads to alpha-amino acid N-carboxy anhydrides . The examples reported constitute the first application of TEMPO in a Baeyer-Villiger reaction and provide a way for peptide coupling from non alpha-amino acid precursors.