Accessing chiral sulfones with an all-carbon quaternary stereocenter via photoinduced asymmetric Truce–Smiles rearrangement and radical sulfur dioxide insertion

Abstract

Chiral sulfones bearing a quaternary stereocenter are privileged structural units that are found in a variety of biologically active products and drug molecules. Herein, we present a photoinduced asymmetric Truce–Smiles rearrangement to access chiral sulfones each bearing an all-carbon quaternary center through radical sulfur dioxide insertion. By using the L-tert-leucine ethyl ester as the chiral auxiliary, the desired chiral sulfones are afforded in good yields with good to excellent stereoselectivities. This protocol features mild reaction conditions, a broad substrate scope, and good stereospecificity.