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Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero-Diels−Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides

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posted on 18.10.2006, 00:00 by Ciby J. Abraham, Daniel H. Paull, Michael T. Scerba, James W. Grebinski, Thomas Lectka
In this Communication, we report a system in which an achiral Lewis acid (activating the diene) works in concert with a chiral nucleophile (dienophile) to effect the first highly enantio- and regioselective catalytic inverse electron demand Diels−Alder [4 + 2] cycloaddition reaction to form biologically active quinoxalinones from ketene enolates and o-benzoquinone diimides in good to excellent yields with >99% ee.