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Synfacts 2008(9): 0942-0942  
DOI: 10.1055/s-2008-1078634
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Asymmetric Decarboxylative [4+2] Cycloaddition

Contributor(s): Mark Lautens, Praew Thansandote
C. Wang, J. A. Tunge*
University of Kansas, Lawrence, USA
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

The authors describe an asymmetric palladium-catalyzed decarboxylative [4+2] cycloaddition of benzoxazinanones and benzylidene malononitriles. The scope is broad with good yields, enantioselectivities, and diastereoselectivities. If the malononitrile is too electron-rich, intramolecular cyclization of the decarboxylated benzoxazinanones forming dihydroquinolines is favored.