Asymmetric Decarboxylative Claisen Rearrangement Reactions of Sulfoximine-Substituted Allylic Tosylacetic Esters

Abstract

Allylic acetate esters containing a variety of N-arylsulfonyl sulfoximines on the acetyl residue have been prepared and submitted to the decarboxylative Claisen rearrangement reaction. Rearranged products were isolated in generally good yields, and diastereoselectivities up to 82:18 have been obtained. The N-(2,4,6-triisopropylphenylsulfonyl)-S-phenyl sulfoximine moiety gave the best selectivity. The stereochemistry of the major isomer was established by X-ray crystallography. A model to explain the stereochemical course of the rearrangement is proposed.