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Synlett 2000; 2000(10): 1470-1472
DOI: 10.1055/s-2000-7628
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Highly Regio- and Enantioselective Heck Reactions of N-Substituted 2-Pyrroline with the New Chiral Ligand BITIANP

Lutz F. Tietze* , Kai Thede
  • *Institut für Organische Chemie der Universität, Tammannstrasse 2, 37077 Göttingen, Germany; Fax + 49 (0) 5 51/39-94 76; E-mail: ltietze@gwdg.de
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Publication Date:
31 December 2000 (online)

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The intermolecular Heck reaction of N-substituted 2-pyrroline 4 with aryl triflates 5a-d in the presence of the chiral ligand (S)-BITIANP 1 gives the N-substituted 5-aryl-2-pyrrolines 6a-d highly regioselectively with excellent enantioselectivity (93-95% ee) and good yields (80-92%). In addition, cyclohexenyl triflate 8 can be transformed with 91% ee.

alkaloids - asymmetric catalysis - chiral ligands - enantioselective Heck reaction - palladium