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Synthesis 1997; 1997(11): 1338-1345
DOI: 10.1055/s-1997-1341
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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 Date:
31 December 2000 (online)

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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