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

Research output: Contribution to journalReview article

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.

Details

Authors
  • Antoine Joosten
  • Andreas K. A. Persson
  • Renaud Millet
  • Magnus Johnson
  • Jan-E. Backvall
Organisations
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Chemical Sciences

Keywords

  • amidopalladation, cyclization, oxazolidinones, oxidation, palladium
Original languageEnglish
Pages (from-to)15151-15157
JournalChemistry: A European Journal
Volume18
Issue number47
Publication statusPublished - 2012
Publication categoryResearch
Peer-reviewedYes