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Synlett 1996; 1996(12): 1215-1217
DOI: 10.1055/s-1996-5702
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Intramolecular 1,3-Dipolar Cycloaddition of Nitrones to Allylsilanes

Wolf Arnold, Peter Mohr*
  • *F. Hoffmann-La Roche Ltd, Pharma Preclinical Research & Development, CH-4070 Basel, Switzerland, FAX +41-61-688 64 59, E-mail peter.mohr@roche.com
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Publication History

Publication Date:
31 December 2000 (online)

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Z- or E-configurated δ- and ℇ-unsaturated nitrones of general formula 1 and 2 have been prepared based on Wittig-methodology, Pd(0)-catalyzed coupling of an E-vinylic bromide or Lindlar-hydrogenation. The Z-derivatives undergo highly stereoselective intramolecular cycloaddition to the respective isoxazolidines.

allylsilane - nitrone - 1,3-dipolar cycloaddition - isoxazolidine - stereoselective

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