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.
A versatile one-pot oxidation-Baeyer-Villiger reaction sequence applied to alpha-hydroxy beta-lactams and promoted by 2,2,6,6-tetramethylpiperidinyl-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.
Palomo
Claudio
C
Departamento de Química Orgánica, Facultad de Química, Universidad del Pais Vasco, Apdo 1072, 20080 San Sebastián, Spain and Organisch-Chemisches Institut der Universität Zürich, Winterthurerstrasse-190, CH-8057, Zürich, Switzerland.
Aizpurua
Jesús M.
JM
Cuevas
Carmen
C
Urchegui
Raquel
R
Linden
Anthony
A