Sulfoxides as stereochemical controllers in intermolecular Heck reactions

The study of a variety of substituted sulfoxides as chiral auxiliaries in i ntermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopent enes with different iodoarenes is reported. In the presence of [Pd(OAc)(2)] /Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and a symmetric inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating o-(N,N-dimethylamino )phenylsulfinyl group. By final removal of the chiral auxiliary, these sulf oxide-stereocontrolled asymmetric Heck processes were applied to the enanti oselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihyd rofurans and cyclopentenes.