Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects
2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 47, 15151-15157 p.Article, review/survey (Refereed) Published
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.
Place, publisher, year, edition, pages
2012. Vol. 18, no 47, 15151-15157 p.
amidopalladation, cyclization, oxazolidinones, oxidation, palladium
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-84775DOI: 10.1002/chem.201202359ISI: 000311111900034OAI: oai:DiVA.org:su-84775DiVA: diva2:582020
FunderSwedish Research Council