title: Influence of the Sulfinyl Group on the Chemoselectivity and pi-Facial Selectivity of Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone.
abstract: Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C(2)-C(3) versus C(5)-C(6) double bonds) is mainly related to the cyclic (on C(5)-C(6)) or acyclic (on C(2)-C(3)) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.
authors.affiliation: Laboratoire de Cristallochimie, UA 424, Université Louis Pasteur, 67070 Strasbourg, France.
authors.forename: M. Carmen
authors.initials: MC
authors.lastname: Carreño
authors.forename: José L.
authors.initials: JL
authors.lastname: García Ruano
authors.forename: Miguel A.
authors.initials: MA
authors.lastname: Toledo
authors.forename: Antonio
authors.initials: A
authors.lastname: Urbano
authors.forename: Cynthia Z.
authors.initials: CZ
authors.lastname: Remor
authors.forename: Valter
authors.initials: V
authors.lastname: Stefani
authors.forename: Jean
authors.initials: J
authors.lastname: Fischer