4.7 Article

Convergent synthesis of azabicycloalkenones using squaric acid as platform

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 16-17, Pages 2493-2500

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ADSC.200606097

Keywords

C-C activation; cycloaddition; heterocycles; rhodium; small ring systems

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The synthesis of azabicycloalkenones bearing a vinylogous amide moiety was achieved by means of the rhodium-catalyzed decarbonylative cycloaddition of cyclobutenediones with a pendant alkene. The starting cyclobutenediones were efficiently prepared from appropriate squaric acid monoesters and N-benzylalkenylamines under microwave heating conditions.

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