title: Catalytic activity of an encaged Verkade's superbase in a base-catalyzed Diels-Alder reaction.
abstract: Organocatalysis in a confined space has been performed through encapsulation of a proazaphosphatrane superbase in a hemicryptophane host. The resulting catalyst displays good to high catalytic activity in the base-catalyzed Diels-Alder reactions investigated. A comparison with the model superbase, which lacks a cavity, shows much higher diastereomeric excess with the encaged proazaphosphatrane for the reaction of 3-hydroxy-2-pyrone with N-methylmaleimide. The use of an encaged superbase as organocatalyst is unprecedented and highlights how the confinement may impact the stereoselectivity.
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, UCBL , 46 allée d'Italie, F-69364 Lyon, France.
authors.forename: Bastien
authors.initials: B
authors.lastname: Chatelet
authors.forename: Véronique
authors.initials: V
authors.lastname: Dufaud
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dutasta
authors.forename: Alexandre
authors.initials: A
authors.lastname: Martinez
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D008301:Maleimides; D011753:Pyrones; C527323:N-methylmaleimide