Synthesis 1997; 1997(11): 1338-1345
DOI: 10.1055/s-1997-1341
feature article
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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
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Publication History

Publication Date:
31 December 2000 (online)

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.