title: The 2-(N,N-Dimethylamino)phenylsulfinyl group as an efficient chiral auxiliary in intramolecular heck reactions
abstract: The synthesis, reactivity, and stereochemical behavior of differently substituted iodoalkenyl alpha,beta-unsaturated sulfoxides in intramolecular Heck reaction is described. Particularly, the 2-(N,N-dimethylamino)phenylsulfinyl group is demonstrated to be an effective chiral auxiliary for the intramolecular Heck reaction of 2-iodo-1,6-(or 1,7)dienes. A desulfinylation sequence removes the auxiliary and yields cyclic compounds of high enantiopurity.
authors.affiliation: Departamento de Quimica Organica, Facultad de Ciencias, Universidad Autonoma de Madrid, 28049 Madrid, Spain.
authors.initials: ND
authors.lastname: Buezo
authors.initials: OG
authors.lastname: Mancheno
authors.initials: JC
authors.lastname: Carretero