Direct Synthesis of Substituted (Z)-Allylic Sulfones by Palladium-Catalyzed Sulfonylation of Vinylethylene Carbonates with Sodium Sulfinates

摘要

A palladium-catalyzed highly stereoselective sulfonylation of vinylethylene carbonates for the precise synthesis of structurally diverse (Z)-allylic sulfones was achieved with excellent regioselectivity and stereoselectivity (Z/E ratio, up to 99 : 1). This protocol used inexpensive sodium sulfinates as sulfonyl sources to construct valuable (Z)-allylic sulfones in good to excellent yields. The controlling experiment suggested that the hydroxyl proton came from the alpha-hydrogen of sulfone group through 1, 5-H shift.