title: Desymmetrization of cyclohexa-2,5-dienes through a diastereoselective protonation-hydroamination cascade.
abstract: [reaction: see text] Intramolecular hydroamination of cyclohexa-2,5-dienes led with high selectivity to the corresponding bicyclic allylic amines. This study demonstrates that the reaction does not proceed through a direct hydroamination of one of the diastereotopic olefins but more likely involves a diastereoselective protonation of a pentadienyl anion, followed by addition of a lithium amide across the double bond of the resulting 1,3-diene, and is concluded by a highly regioselective protonation of the final allylic anion.
authors.affiliation: University Bordeaux-1, Laboratoire de Chimie Organique et Organométallique, 351, Cours de la Libération, 33405 Talence Cedex, France.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Lebeuf
authors.forename: Frédéric
authors.initials: F
authors.lastname: Robert
authors.forename: Kurt
authors.initials: K
authors.lastname: Schenk
authors.forename: Yannick
authors.initials: Y
authors.lastname: Landais