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Synlett 1990; 1990(2): 97-98
DOI: 10.1055/s-1990-20999
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Highly Diastereoselective Claisen Rearrangements of N-Silyl Ketene N, O-Acetals Generated from Allyl N-Phenylimidates

Peter Metz* , Cornelia Mues
  • *Organisch-chemisches Institut der Universität Münster, Corrensstrasse 40, D-4400 Münster, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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N-Silyl ketene N,O-acetals generated from prochiral allyl N-phenylimidates by deprotonation and subsequent N-silylation undergo diastereoselective Claisen rearrangements to give γ,δ-unsaturated amides. Double-bond substituents larger than hydrogen and vicinal to the oxygen atom of the imidates give rise to highly stereoselective rearrangemants by efficient suppression of the reaction pathway via a boat transition state.