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

摘要

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.