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

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@article{45b3c99207e94d199b03ecb4fc42c1c5,
title = "Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects",
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 beta-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.",
keywords = "amidopalladation, cyclization, oxazolidinones, oxidation, palladium",
author = "Antoine Joosten and Persson, {Andreas K. A.} and Renaud Millet and Magnus Johnson and Jan-E. Backvall",
year = "2012",
doi = "10.1002/chem.201202359",
language = "English",
volume = "18",
pages = "15151--15157",
journal = "Chemistry: A European Journal",
issn = "1521-3765",
publisher = "Wiley-VCH Verlag",
number = "47",

}