Faculté des sciences

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

Franz, Andreas ; Eschler, Pierre-Yves ; Neier, Reinhard

In: Tetrahedron, 1996, vol. 53, no. 35, p. 11643-11656

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. More

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    Summary
    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.