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Synfacts 2008(8): 0804-0804
DOI: 10.1055/s-2008-1077946
DOI: 10.1055/s-2008-1077946
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Inverse Diels-Alder Proline-Catalyzed Route to 1,2,4,5-Tetrazines
H. Xie, L. Zu, H. R. Oueis, H. Li, J. Wang, W. Wang*
University of New Mexico, Albuquerque, USA
Further Information
Publication History
Publication Date:
23 July 2008 (online)
Significance
The well-known inverse electron demand Diels-Alder reaction of ketones with 1,2,4,5-tetrazines using solid support anchored l -proline organocatalysis is reported. The normal mechanism via enamine cycloaddition to the tetrazine followed by elimination and recovery of the proline catalyst is proposed. The scope of the reaction was modestly tested for the ketone component but is clearly based on commercially available tetrazine derivatives.