1433206-33-7Relevant articles and documents
Palladium(II)-catalyzed oxidative cyclization of allylic tosylcarbamates: Scope, derivatization, and mechanistic aspects
Joosten, Antoine,Persson, Andreas K. ?.,Millet, Renaud,Johnson, Magnus T.,B?ckvall, Jan-E.
supporting information, p. 15151 - 15157 (2013/01/15)
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.