title: Formal Asymmetric Organocatalytic [3+2] Cyclization between Enecarbamates and 3-Indolylmethanols: Rapid Access to 3-Aminocyclopenta[b]indoles.
abstract: A highly enantio- and diastereoselective synthesis of 3-aminocyclopenta[b]indoles has been developed through formal [3+2] cycloaddition reaction of enecarbamates and 3-indolylmethanols. This transformation is catalyzed by a chiral phosphoric acid that achieves simultaneous activation of both partners of the cycloaddition. Mechanistic data are also presented that suggest that the reaction occurs through a stepwise pathway.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Sud, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-69077247.
authors.forename: Clément
authors.initials: C
authors.lastname: Lebée
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Sud, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-69077247.
authors.forename: Antti O
authors.initials: AO
authors.lastname: Kataja
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Sud, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-69077247.
authors.forename: Florent
authors.initials: F
authors.lastname: Blanchard
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Sud, 91198 Gif-sur-Yvette Cedex (France), Fax: (+33) 1-69077247. geraldine.masson@cnrs.fr.
authors.forename: Géraldine
authors.initials: G
authors.lastname: Masson
keywords: asymmetric synthesis; chirality; cycloaddition; enamide; iminium; indoles