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Preparation of N-alkylketene-N-butadienyl-N,O-silyl acetals

1996, Franz, Andreas, Eschler, Pierre Yves, Tharin, Manuel, Stoeckli-Evans, Helen, Neier, Reinhard

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 dienamides. The ketene acetals are obtained free of base and free of salts. They are stable and can be stored at - 20 degrees C. The new dienes are useful reagents for tandem reactions.

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

1996, Franz, Andreas, Eschler, Pierre-Yves, Tharin, Manuel, Stoeckli-Evans, Helen, Neier, Reinhard

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.

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The preparation and the cascade reactions of N-butadienyl-N-alkylketene N,O-tert-butyldimethylsilyl acetals

1996, Franz, Andreas, Eschler, Pierre Yves, Tharin, Manuel, Neier, Reinhard

The preparation of N-butadienyl-N-alkylketene N,O-tert-butyldimethylsilyl acetals (11a-d) from readily available starting materials is described. The cascade Diels-Alder reaction followed by acylation of these ketene acetals yields bicyclic and tricyclic products 7, 13a,b and 14c,d with high diastereoselectivity. Copyright (C) 1996 Elsevier Science Ltd

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An Unexpected Tandem Reaction of N-Butadienyl-N-Alkylketene-N, O-Silylacetals

1996, Franz, Andreas, Eschler, Pierre Yves, Tharin, Manuel, Neier, Reinhard, Rzepa, H.J., Leach, C., Goodman, J.M.