Solid-phase synthesis of cleavable N-arylmaleimides: applications in 1,3-dipolar cycloaddition and in thiol scavenging.

[reaction: see text]. An efficient solid-phase synthesis of polymer-supported N-arylmaleimides has been developed. Various N-arylmaleimidobenzoic acids (MBA) were elaborated onto Rink and SASRIN resins by reaction of the aniline precursors with maleic anhydride followed by facile cyclative dehydration of the resulting maleimic acids. Applications of these acid-cleavable MBA resins in the solid-phase synthesis of highly decorated pyrrolidines and as thiol scavengers are presented.