Catalytic Activity of an Encaged Verkade’s Superbase in a Base-Catalyzed Diels–Alder Reaction - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2014

Catalytic Activity of an Encaged Verkade’s Superbase in a Base-Catalyzed Diels–Alder Reaction

Résumé

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.
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Dates et versions

hal-01121295 , version 1 (28-02-2015)

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Bastien Chatelet, Véronique Dufaud, Jean-Pierre Dutasta, Alexandre Martinez. Catalytic Activity of an Encaged Verkade’s Superbase in a Base-Catalyzed Diels–Alder Reaction. Journal of Organic Chemistry, 2014, 79 (18), pp.8684-8688. ⟨10.1021/jo501457d⟩. ⟨hal-01121295⟩
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