Stereoselective dioxygenation of a racemic tryptophan derivative catalysed by chiral manganese porphyrins

Abstract

The first asymmetric dioxygenation reactions of the racemic tryptophan derivatives, N-acetyl-L-(+)-[and D-(–)]-tryptophan methyl ester, are reported, in which predominant generation of methyl 2-D-acetoamido-3-(2-formamidobenzoyl)propionate has been acheived in 23.3% enantiometric excess in the cataytic system using the manganese complex of α,α,α,α-tetrakis[O-L(–)-camphanoylamido) phenyl]porphyrin.