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Domino 1,4-Addition/Carbocyclization Reaction through a Radical–Polar Crossover Reaction

Authors

  • Fabrice Denes,

    1. Laboratoire de Chimie Organique, UMR 7611, Bte 183, Tour 44-45 2ème étage, Université Pierre et Marie Curie, 4 Place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7567
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  • Fabrice Chemla Prof.,

    1. Laboratoire de Chimie Organique, UMR 7611, Bte 183, Tour 44-45 2ème étage, Université Pierre et Marie Curie, 4 Place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7567
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  • Jean F. Normant

    1. Laboratoire de Chimie Organique, UMR 7611, Bte 183, Tour 44-45 2ème étage, Université Pierre et Marie Curie, 4 Place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7567
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  • Thanks are due to Prof. Philippe Renaud (University of Bern) for helpful discussions.

Abstract

original image

Radical processes explain the reactivity and selectivity observed in a one-pot, two- or three-component domino reaction, which consists of 1,4-addition, carbocyclization, and quenching with electrophiles. This radical–polar crossover reaction leads stereoselectively to 3,4-disubstituted 3-methoxycarbonylpyrrolidines (see scheme).

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