The reversed Kenner linker: a new safety-catch linker for the preparation of N-alkyl sulfonamides

Abstract

A new strategy for the solid-phase synthesis of sulfonamides is described. The Kenner safety-catch strategy has been modified such that the carboxylic acid component remains attached to the solid support while the sulfonamide portion is released into solution. An initial demonstration of the scope of this strategy is presented, along with an analysis of the cleavage characteristics and extension to more elaborate products via Suzuki reaction and thiazolidinone synthesis. Reaction: see text.