Synthesis of Optically Active 9-Methoxy-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarbox-amide Derivatives via Asymmetric Diels-alder Reaction of a Chiral Sulfinylmaleimide with 9-Methoxyanthracene

The title compounds 6 and 7 have proved to be adequate rigid models to evaluate the ability of the sulfinyl group to control the diastereoselectivity of the [4 + 2] cycloadditions of cyclopentadiene on the ene-dione moiety. The results of thermal and Lewis acid-catalyzed reactions allowed us to establish that both reactivity and endo/exo selectivity were modulated by the presence of the sulfinyl group, the endo-anti-endo or the exo-anti-endo bisadducts being obtained as major products depending on experimental conditions. The role of the association between the SOTol group and several Lewis acids (BF(3).OEt(2), Eu(fod)(3), ZnBr(2)), which shifted the conformational equilibrium around the C-S bond, was used to explain the stereochemical course of the cycloadditions mainly controlled by steric factors. The synthesis of the exo-anti-endo bisadduct 5 was described for the first time.

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Studies of Diastereoselectivity in Diels−Alder Reactions of (S)S-4a,5,8,8a-Tetrahydro-5,8-methane-2-(p-tolylsulfinyl)-1,4-naphtho- quinones with Cyclopentadiene

Carreño

Ruano

Urbano

et al. 1996

J. Org. Chem.

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Synthesis of Optically Active 9-Methoxy-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarbox-amide Derivatives via Asymmetric Diels-alder Reaction of a Chiral Sulfinylmaleimide with 9-Methoxyanthracene

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Studies of Diastereoselectivity in Diels−Alder Reactions of (S)S-4a,5,8,8a-Tetrahydro-5,8-methane-2-(p-tolylsulfinyl)-1,4-naphtho- quinones with Cyclopentadiene

Studies of Diastereoselectivity in Diels−Alder Reactions of (S)S-4a,5,8,8a-Tetrahydro-5,8-methane-2-(p-tolylsulfinyl)-1,4-naphtho- quinones with Cyclopentadiene

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