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Synlett 1998; 1998(1): 53-54
DOI: 10.1055/s-1998-3124
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Enantioselective Allylic Substitution Using a Novel (Phosphino-α-d-glucopyrano-oxazoline)palladium Catalyst

Björn Gläser* , Horst Kunz
  • *Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, J. J. Becherweg 18-20, D-55099 Mainz, Germany; Fax (Int.) 49 61 31 39 47 86; E-mail: hokunz@goofy.zdv.uni-mainz.de
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Publikationsdatum:
31. Dezember 2000 (online)

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A novel enantiomerically pure 2-[2-(diphenylphosphino)phenyl]-4,5-(2-deoxy-α-d-glucopyrano)-oxazoline ligand (6) was prepared from glucosamine (1). The stereodifferentiating potential of the ligand 6 was demonstrated in palladium-catalyzed intermolecular allylic substitutions of symmetrically and non-symmetrically substituted allyl acetates which give products in high yields and high enantioselectivity (up to 98% ee).

enantioselective catalysis - palladium-catalyzed allylation - P,N-ligand - carbohydrate-derived ligand - glucosamine