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Intramolecular Diels-Alder reactions of cyclopropenone ketals.

ABSTRACT: The first intramolecular cycloaddition reactions of cyclopropenone ketals with tethered electron-deficient, electron-rich, and neutral 1-substituted dienes are reported, constituting inverse electron demand, normal, and neutral Diels-Alder reactions, that provide exclusively the exo [4 + 2] cycloaddition products without the intervention of [1 + 2], [3 + 2], or [3 + 4] cycloadducts in reactions whose courses do not depend on the reaction conditions, the diene activating substituent, or the nature of the tethering.

SUBMITTER: Patel PR

PROVIDER: S-EPMC2912946 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Intramolecular Diels-Alder reactions of cyclopropenone ketals.

Patel Paresma R PR Boger Dale L DL

Organic letters 20100801 15

The first intramolecular cycloaddition reactions of cyclopropenone ketals with tethered electron-deficient, electron-rich, and neutral 1-substituted dienes are reported, constituting inverse electron demand, normal, and neutral Diels-Alder reactions, that provide exclusively the exo [4 + 2] cycloaddition products without the intervention of [1 + 2], [3 + 2], or [3 + 4] cycloadducts in reactions whose courses do not depend on the reaction conditions, the diene activating substituent, or the natur ...[more]

PMID: 20614867

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