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Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide.
Journal article

Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide.

  • Corminboeuf O Department of Chemistry and Biochemistry, University of Berne, Freiestrasse 3 CH-3000 Berne 9, Switzerland.
  • Renaud P
  • 2002-05-10
Published in:
  • Organic letters. - 2002
English [reaction: see text] The use of hydroxamic acids as templates for Lewis acid catalyzed enantioselective Diels-Alder reactions has been examined. A very simple chiral Lewis acid, prepared by mixing optically pure binaphthol with 3 equiv of trimethylaluminum, catalyzes the [4 + 2] cycloaddition of N-hydroxy-N-phenylacrylamide with cyclopentadiene at 0 degrees C in high yield (>96%) and with a fairly good level of enantioselectivity (91% ee). Facile conversion of the products to the corresponding alcohols or aldehydes makes the hydroxamic acid intermediates particularly useful.
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  • English
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https://sonar.ch/global/documents/192115
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