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Synlett 1998; 1998(3): 277-279
DOI: 10.1055/s-1998-1623
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Domino Reactions of a Double δ,ℇ-Unsaturated Dioxime: Competition between Two Intramolecular Cycloaddition Pathways

Subramanian Baskaran* , Hans Günter Aurich
  • *Fachbereich Chemie, Philipps-Universität Marburg, D-35032 Marburg, Germany; Fax +49 (0) 64 21 28 89 17
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Publication Date:
31 December 2000 (online)

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Reduction of compound 1 with DIBAL-H followed by treatment of the reaction mixture with hydroxylamine affords the dioxime 3 along with the monoximes 6 and 7. On refluxing in toluene, 3 undergoes a conversion to the polycyclic compounds 5 and 10 by two different cycloaddition processes. The stereochemical course of these domino reactions is discussed.

oximes - 1,2-prototropy - 1,3-dipolar cycloaddition - 1,3-azaprotio cyclotransfer - stereoselectivity