L-methionine oxidation : novel and unanticipated transformations with 4-^tbutyl iodoxybenzene

Abstract

4-^tButyl iodoxybenzene transforms Bz-Met-OMe to products arising from, S oxidation and C-H insertion followed by degradation. Z-Met (sulfoxide)-OMe is very effective in bringing about ester hydrolysis via intra-molecular attack. The S oxidation to sulfoxides and then to sulfones can be monitored and controlled, proceeds with chiral retention, affects neither the peptide bond nor the protecting groups and has been further illustrated with, Z-Gly-Met-OMe, Z-Met-OMe and Z-S(benzyl)-Cys-OMe.