Faculté des sciences

Preparation of N-Alkylketene-N-Butadienyl-N,O-Silyl Acetals

Franz, Andreas ; Eschler, Pierre-Yves ; Tharin, Manuel ; Stoeckli-Evans, Helen ; Neier, Reinhard

In: Synthesis, 1996, vol. 10, p. 1239-1245

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. Plus

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    Summary
    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.