title: Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles: Diels-Alder reactions with furan and acyclic dienes.
abstract: The dienophilic behavior of the sulfilimine 2, synthesized from (Z)-3-p-tolylsulfinylacrylonitrile 1, in its Diels-Alder reactions with furan and acyclic dienes has been investigated. A complete pi-facial selectivity for 2, opposite to that observed from its precursor 1, is the main feature of all these cycloadditions. Moreover, the high exo selectivity observed in reactions of 2 with furan (not observed for 1) contrasts with the almost complete endo selectivity with other cyclic and acyclic dienes. Additionally, the opposite regioselectivities obtained for 2 with Dane's diene and 1-substituted butadienes (not observed for 1) are also noteworthy. This behavior allows dienophiles 1 and 2 to be considered as complementary precursors from a synthetic point of view.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
authors.forename: José L
authors.initials: JL
authors.lastname: García Ruano
authors.forename: Carlos
authors.initials: C
authors.lastname: Alemparte
authors.forename: Fernando R
authors.initials: FR
authors.lastname: Clemente
authors.forename: Lorena
authors.initials: L
authors.lastname: González Gutiérrez
authors.forename: Ruth
authors.initials: R
authors.lastname: Gordillo
authors.forename: Ana M
authors.initials: AM
authors.lastname: Martín Castro
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Rodríguez Ramos