Unique oxidation reaction of amides with pyridine-N-oxide catalyzed by ruthenium porphyrin: Direct oxidative conversion of N-acyl-L-proline to N-acyl-L-glutamate

R Ito, N Umezawa, T Higuchi

Index: Ito, Rina; Umezawa, Naoki; Higuchi, Tsunehiko Journal of the American Chemical Society, 2005 , vol. 127, # 3 p. 834 - 835

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Citation Number: 43

Abstract

Oxidations of alkanes, alkenes, and aromatic rings with pyridine N-oxides are efficiently catalyzed by ruthenium porphyrins under mild conditions. We show here that the oxidation of N-acyl cyclic amines with RuIVtetraarylporphyrin dichloride-2, 6-substituted pyridine N- oxides directly gives N-acyl amino acids in modest to good yield via oxidative CN bond cleavage. N-Acylpyrrolidines and N-acylpiperidines were converted to N-acyl-γ- ...