Synthesis of Stereoselective Multifused Cyclic Compounds via Palladium-Catalyzed C3-Allylative Dearomatization

Abstract

In this study, Pd-catalyzed enantioselective C3-allylative dearomatization is performed, which proceeds via dearomative [3 + 2] cycloaddition involving quinolinium zwitterions and vinyl cyclopropanes. This protocol is significant for the synthesis of complex, multifused cyclic compounds characterized by meticulously controlled multistereogenic centers using π-allyl palladium species. The method developed herein presents an approach to overcoming the challenge of achieving stereoselective C3functionalization. The SEGPHOS ligand plays an integral role in this process by improving both the conversion rates and stereoselectivity. Our investigation also underscores the versatility of this methodology by demonstrating its potential for the construction of stereocontrolled fused N-cyclic systems. The results of this study lay the foundation for the further exploration and refinement of asymmetric dearomatization aimed at the strategic construction of stereoselective N-heterocyclic compounds.