Download PDF
Synthesis 1997; 1997(11): 1338-1345
DOI: 10.1055/s-1997-1341
feature article
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Enantioselective Heck Reactions Catalyzed by Chiral Phosphinooxazoline-Palladium Complexes

Olivier Loiseleur, Masahiko Hayashi, Norbert Schmees, Andreas Pfaltz*
  • *Institut für Organische Chemie, Universität Basel, St.Johanns-Ring 19, CH-4056 Basel, Switzerland; Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany, Fax +49(208)3062992; E-mail: pfaltz@mpi-muelheim.mpg.d
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Palladium complexes with chiral phosphinooxazoline ligands are efficient catalysts for enantioselective Heck reactions with aryl or alkenyl triflates and cyclic alkenes. In the arylation and alkenylation of 1,2-dihydrofuran, cyclopentene, 2,3-dihydro-4H-pyran, 4,7-dihydro-1,3-dioxepin, and N-methoxycarbonyl-2,3-dihydropyrrole high yields and good to excellent enantioselectivities have been obtained. In contrast to analogous (BINAP)Pd-catalyzed reactions, isomerization of the products by C-C double bond migration was essentially not observed.

Heck reaction - asymmetric catalysis - P,N-ligands - oxazolines - Pd catalysts

      >