Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero-Diels−Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides
- 21 September 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (41) , 13370-13371
- https://doi.org/10.1021/ja065754d
Abstract
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.Keywords
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