Palladium-catalyzed nucleophilic allylic substitution of Morita–Baylis–Hillman adducts with enamines: Synthesis of 1,5-dicarbonyl compounds |
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| Institution: | 1. Université de Tunis EL Manar, Faculté des sciences, Laboratoire de chimie organique structurale, Campus universitaire, 2092 Tunis, Tunisia;2. Université de Toulouse-3, Université Paul-Sabatier, Faculté des sciences pharmaceutiques, Laboratoire des IMRCP, UMR CNRS 5623, 35, chemin des Maraichers, 31062 Toulouse cedex 09, France |
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| Abstract: | An efficient nucleophilic allylic substitution of a variety of Morita–Baylis–Hillman adducts with enamines catalyzed by Pd(OAc)2 in the presence of ZnBr2 as a promoter is described in the present study. The reaction gives SN2-type 1,5-dicarbonyl compounds that may subsequently undergo an intramolecular conjugate addition onto the enone moiety affording the corresponding 1,4-adducts. All the synthesized compounds have been isolated in moderate to good yields and fully characterized. |
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| Keywords: | Allylic substitution Palladium Enamine 1 5-Dicarbonyl compounds Morita–Baylis–Hillman Conjugate addition |
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