Phosphines catalyzed nucleophilic addition of azoles to allenes: synthesis of allylazoles and indolizines |
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Authors: | David Virieux Anne-Françoise Guillouzic Henri-Jean Cristau |
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Institution: | Laboratoire de Chimie Organique, UMR 5076, Ecole Nationale Supérieure de Chimie de Montpellier 8, rue de l'Ecole Normale, 34296 Montpellier cedex 5, France |
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Abstract: | Triphenylphosphine was used as nucleophilic catalyst for umpolung addition of azoles to electron-deficient allenes. This strategy offers a simple and efficient method for functional allylation of azoles under neutral conditions and affords heterocyclic substituted Michael olefins. Furthermore, this catalytic methodology has been extended to addition-cyclization reactions between electron-deficient allenes or alkynes and pyrrole-2-carboxaldehyde in the presence of catalytic amount of tributylphosphine. In such conditions, substituted indolizine-7-carboxylates are easily obtained. |
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Keywords: | Phosphines Nucleophilic catalysis Allylation Azoles Indolizines |
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