Solvent-Controlled Enantioselective Allylic C–H Alkylation of 2,5-Dihydrofuran via Synergistic Palladium/Nickel Catalysis

Abstract

Enantioenriched, substituted tetrahydrofuran skeletons extensively occur in natural products, bioactive targets, and organic frameworks. The rapid and diverse synthesis of these tetrahydrofuran molecules is highly desired yet challenging. Herein, we present a practical synthetic strategy for asymmetric allylic C–H bond functionalization of oxyheterocyclic alkenes by making use of the synergistic catalysis of achiral Pd complex and chiral N,N′-dioxide-Ni(II) catalyst. Notably, the chemodivergent synthesis of allylic C–H alkylated products and hydroalkylated products was readily achieved in good outcomes via the regulation of solvents. Furthermore, the post-transformation of these functionalized 2,5-dihydrofurans provides an innovative synthetic route to access tetrahydrofuran skeleton compounds containing multiple stereocenters.