864443-52-7Relevant articles and documents
Asymmetric decarboxylative claisen rearrangement reactions of sulfoximine-substituted allylic tosylacetic esters
Craig, Donald,Grellepois, Fabienne,White, Andrew J. P.
, p. 6827 - 6832 (2007/10/03)
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.