Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2-derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile-assisted ring-opening step following an SNi pathway, and a 5-exo-tet cyclization, thus leading to heterocyclic scaffolds.
Substrate Controlled Product Divergence in CO2 Conversion to Heterocyclic Products
Angew. Chem. Int. Ed. 2016, 55, 3972-3976.