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

An asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates and beta-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.