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

Författare

  • Antoine Joosten
  • Andreas K. A. Persson
  • Renaud Millet
  • Magnus Johnson
  • Jan-E. Backvall

Summary, in English

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.

Publiceringsår

2012

Språk

Engelska

Sidor

15151-15157

Publikation/Tidskrift/Serie

Chemistry: A European Journal

Volym

18

Issue

47

Dokumenttyp

Artikel i tidskrift

Förlag

Wiley-Blackwell

Ämne

  • Chemical Sciences

Nyckelord

  • amidopalladation
  • cyclization
  • oxazolidinones
  • oxidation
  • palladium

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 1521-3765