Development of ortho-nosylOXY as a novel coupling reagent for peptide synthesis and related organic transformations

Abstract

We developed a reagent coupling reagent ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (ortho-NosylOXY) and its application for the synthesis of amides, esters, peptides, hydroxamates, N-protected amino acid based benzoxazoles & benzothiazoles and nitriles. The whole structure of the thesis is depicted in scheme 1. Firstly, we have developed a method for the synthesis of o-NosylOXY and its application for racemization free synthesis of amides and peptides. Secondly, we established a method for racemization free synthesis of ester and hydroxamates using o-NosylOXY. Thirdly, we illustrated synthesis of benzoxazole and benzothiazole from carboxylic acid and N-protected amino acid by o-NosylOXY. Fourthly, we demonstrated the application of o-NosylOXY for nitrile synthesis. Finally, we described the synthesis of amide/lactam from ketoxime via Beckmann rearrangement and o-NosylOXY as a organocatalyst.