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 |
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| Authors: | Palomo Claudio Aizpurua Jesús M Cuevas Carmen Urchegui Raquel Linden Anthony |
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| Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad del Pais Vasco, Apdo 1072, 20080 San Sebastián, Spain and Organisch-Chemisches Institut der Universit?t Zürich, Winterthurerstrasse-190, CH-8057, Zürich, Switzerland. |
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| Abstract: | 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. |
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