Synlett 1989; 1989(1): 34-35
DOI: 10.1055/s-1989-34704
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Silica Gel Catalyzed Cyclizations of Enones and Double Michael Additions of Vinylogous Amides: Efficient Synthesis of Bicyclo[2.2.2]octanones and Bicyclo-Hydrocarbazolones

Dieter Schinzer* , Markus Kalesse
  • *Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, D-3000 Hannover 1, Federal Republic of Germany
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Publication History

Publication Date:
26 February 2002 (online)

Mixed ketene acetals of enones of type 2 undergo stereoselective cyclizations on a short column of silica gel, to yield bicyclo[2.2.2]octanones of type 3. Enolates of vinylogous amides of types 6 and 8 cyclize directly upon reaction with methyl acrylate at -78 °C to form bicyclic ß-amino ketones of types 7 and 9.