Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects - Archive ouverte HAL Access content directly
Journal Articles Chemistry - A European Journal Year : 2012

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

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1
Antoine Joosten

Abstract

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.

Dates and versions

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

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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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