An Asymmetric Allylic Alkylation–Smiles Rearrangement–Sulfinate Addition Sequence to Construct Chiral Cyclic Sulfones

An asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates and β-keto sulfones was investigated by the catalysis of modified cinchona alkaloids, whose products underwent a Smiles rearrangement–sulfinate addition cascade to furnish highly functionalized five-membered cyclic sulfones in moderate to excellent enantioselectivity and good diastereoselectivity after treatment with DBU.