Rh(III)-catalyzed three-component coupling of C–H bond substrates, bridged bicyclic alkenes, and dioxazolones

Bridged bicyclic structures are common motifs in drugs and drug candidates, with [2.2.1]- and [3.2.1]-bridged frameworks being especially prevalent. A one pot three component method to prepare syn-1,2-disubstituted bridged bicyclic compounds from readily available C–H bond substrates, bridged bicyclic alkenes, and dioxazolones is described. This reaction proceeds by C–H activation by a Cp*Rh(III) catalyst followed by alkene insertion and then amidation with the dioxazolone. Evaluation of reaction scope and exploration of asymmetric catalysis with different types of chiral Rh(III) complexes will be presented. Preliminary investigation using other classes of alkene partners will also be reported.