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Synthesis 1996; 1996(10): 1239-1245
DOI: 10.1055/s-1996-4359
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Preparation of N-Alkylketene-N-Butadienyl-N,O-Silyl Acetals

Andreas Franz, Pierre-Yves Eschler, Manuel Tharin, Helen Stoeckli-Evans, Reinhard Neier*
  • *Institut de Chimie de l’Université de Neuchâtel, CH-2000 Neuchâtel, Switzerland, Fax +41(38)232511; E-mail reinhard.neier@ich.unine.ch
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Publication Date:
31 December 2000 (online)

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The synthesis of a series of dienamides 5a-j using Oppolzer’s method is described. Using Rathke’s method the ketene N,O-silyl acetals 6a-j can be obtained in good yield from the corresponding dienamines. The ketene acetals are obtained free of base and free of salts. They are stable and can be stored at -20°C. The new dienes are useful reagents for tandem reactions.

dienamides - synthesis of ketene N,O-tert-butyldimethylsilyl acetals - Diels-Alder reactions - tandem reactions - domino reaction - cascade reactions

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