Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition |
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| Authors: | Baslé Olivier Porcel Susana Ladeira Sonia Bouhadir Ghenwa Bourissou Didier |
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| Affiliation: | Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse, France. |
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| Abstract: | Phosphine-boronates R(2)P(o-C(6)H(4))B(OR')(2) have been evaluated as bifunctional organocatalysts for the Michael addition of malonate pronucleophiles to methylvinylketone. The presence of the Lewis acidic boron center adjacent to phosphorus significantly improves catalytic performance. Isolation and complete characterization of a key intermediate, namely a β-phosphonium enolate, substantiate the role of the Lewis acidic moiety in the catalytic process. |
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