Mal-(1R,2S,3R,4S)-himic acid-alkyne

Mal-(1R,2S,3R,4S)-himic acid-alkyne (Compound 3) undergoes highly selective CuAAC click chemistry at its alkyne group, with >99% conversion to the triazole product in individual reactions and full conversion within 1 h in a sequential one-pot setup, with minimal side product formation^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes highly selective thiol-Michael click chemistry at its maleimide group, with >99% conversion to the thioether product in individual reactions and complete consumption in a sequential one-pot setup, with low levels of norbornene-directed side product formation^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes highly selective iEDDA click chemistry at its norbornene double bond, with >99% conversion to dihydropyridazine/pyridazine products in individual reactions and complete consumption in a sequential one-pot setup, with reaction rate dependent on solvent choice^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes simultaneous one-pot triple click chemistry resulting in <10% yield of the targeted triple-click product, as copper catalyst deactivation inhibits the CuAAC reaction despite quantitative completion of iEDDA and thiol-Michael reactions^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes sequential one-pot triple click chemistry, performed in the order CuAAC, iEDDA, thiol-Michael, resulting in >99% conversion to the targeted triple-click product with 95% isolated yield, with complete selective consumption of all three clickable functional groups and no detectable side reactions^[1].

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