Exploring Pd/Al₂O₃ Catalysed Redox Isomerisation of Allyl Alcohol as a Platform to Create Structural Diversity

We report our results on exploiting the different reactivities present in the catalytic cycle of the Pd/Al₂O₃ catalyzed redox isomerization of allyl alcohol. We show that the reactivity of allyl alcohol derived acrolein and enol can be involved in further cascade reactions leading to a diverse set of products. While the oxidation product acrolein can react via Michael and oxa-Michael reactions, the isomerization product enol can be readily involved in aldol condensation processes. Salicylaldehydes, that are able to react on their electrophilic carbonyl and nucleophilic OH-groups with allyl alcohol derived enol and acrolein, respectively, are used to explore conditions where the structure of the product heterocycles can be controlled.