Solid phase Diels–Alder/retro Diels–Alder reactions. A new method for traceless linker strategy

A resin-bound furan has been efficiently synthesized from Merrifield resin. This new polymer reacts with an acetylenic dienophile to afford a thermally stable Diels–Alder adduct. Transformation of the adduct by Michael reaction with thiophenol has allowed an easy retro Diels–Alder reaction. This ‘safety-catch’ procedure leads to the formation of a chemically and stereochemically pure alkene and to the regeneration of the polymer-bound furan.