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Synfacts 2007(1): 0072-0072
DOI: 10.1055/s-2006-955718
DOI: 10.1055/s-2006-955718
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Bifunctional Inverse Electron Demand Hetero-Diels-Alder Reactions
C. J. Abraham, D. H. Paull, M. T. Scerba, J. W. Grebinski, T. Lectka*
Johns Hopkins University, Baltimore, USA
Further Information
Publication History
Publication Date:
15 December 2006 (online)
Significance
The authors report an inverse-electron-demand hetero-Diels-Alder reaction of ketene enolates and o-benzoquinone diimides. The products of this reaction are the biologically and medicinally important quinoxalinones. The reaction proceeded with high yield and essentially perfect enantioselectivity with various substituted o-benzoquinone diimides as well a variety of ketenes. The authors demonstrated the power of this method by the simple synthesis of a compound which shows strong antiviral activity against HIV as well as compound 1, which is an inhibitor of cholesteryl ester transfer protein.