Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects - Normandie Université Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2012

Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects

Antoine Joosten

Résumé

A highly selective oxidative palladium(II)‐catalyzed (Wacker‐type) cyclization of readily available allylic tosylcarbamates is reported. This operationally simple catalytic reaction furnishes tosyl‐protected vinyl‐oxazolidinones, common precursors to syn‐1,2‐amino alcohols, in high yield and excellent diasteroselectivity (>20:1). It is demonstrated that both stoichiometric amounts of benzoquinone (BQ) as well as aerobic reoxidation (molecular oxygen) is suitable for this transformation. The title reaction is shown to proceed through overall trans‐amidopalladation of the olefin followed by β‐hydride elimination. This process is scalable and the products are suitable for a range of subsequent transformations such as: kinetic resolution (KR) and oxidative Heck‐, Wacker‐, and metathesis reactions.

Domaines

Chimie

Dates et versions

hal-02548582 , version 1 (20-04-2020)

Identifiants

Citer

Antoine Joosten, Andreas Persson, Renaud Millet, Magnus Johnson, Jan-E. Bäckvall. Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects. Chemistry - A European Journal, 2012, 18 (47), pp.15151-15157. ⟨10.1002/chem.201202359⟩. ⟨hal-02548582⟩

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