Abstract
Abstract To study the intramolecular Diels–Alder cycloadditon of 2 H -chromen-2-one as a diene, a series of chiral N -allyl- N -benzylamides that contain a 2 H -chromen-2-one moiety were designed for the synthesis of benzo[ f ]isoindol-1-ones via an intramolecular Diels–Alder and a subsequent retro-Diels–Alder cycloaddition with the expulsion of CO 2 . Both the yield (80%–89%) and absolute stereocontrol of the tandem reaction were high when an electron-withdrawing group was attached to the dienophile. The double bond in the styrene substructure remained in the products could be further derivatized by dihydroxylation.
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