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Catalytic, enantioselective bifunctional inverse electron demand hetero-diels-alder reactions of ketene enolates and o-benzoquinone diimides
Journal article

Catalytic, enantioselective bifunctional inverse electron demand hetero-diels-alder reactions of ketene enolates and o-benzoquinone diimides

Ciby J Abraham, Daniel H Paull, Michael T Scerba, James W Grebinski and Thomas Lectka
Journal of the American Chemical Society, Vol.128(41), pp.13370-13371
2006
PMID: 17031945

Abstract

Chemistry Exact sciences and technology General and physical chemistry Noncondensed benzenic compounds Preparations and properties Organic Chemistry
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.

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