title: Sulfoxides as stereochemical controllers in intermolecular Heck reactions.
abstract: The study of a variety of substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)2]/Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and asymmetric 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 sulfoxide-stereocontrolled asymmetric Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes.
authors.affiliation: Departamento de Química Orgánica, facultad de Ciencias, Universidad Autónoma de Madrid, Spain.
authors.forename: N
authors.initials: N
authors.lastname: Díaz Buezo
authors.forename: J C
authors.initials: JC
authors.lastname: de la Rosa
authors.forename: J
authors.initials: J
authors.lastname: Priego
authors.forename: I
authors.initials: I
authors.lastname: Alonso
authors.forename: J C
authors.initials: JC
authors.lastname: Carretero