Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles |
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Authors: | Marco Bandini Andrea Gualandi Magda Monari Alessandro Romaniello Diego Savoia Michele Tragni |
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Institution: | Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum, Università di Bologna, via Selmi 2, 40126 Bologna, Italy |
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Abstract: | The recent booming of gold catalysis has demonstrated that unprecedented transformations can be realized in a highly selective manner. Moreover, due to the growing availability of chiral organic ligands, gold-catalysis can be considered as one of most dynamic hot spots in asymmetric synthesis. However, in this context, the use of non-activated olefinic C-C double bonds is still largely unexplored due to the intrinsic inertness of C C (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by π-electrophilic activations. Allylic alcohols have been demonstrated to be feasible “surrogates” of non-activated alkenes for the enantioselective allylic alkylation of indoles catalyzed by chiral gold(I) complexes. In this investigation, a full account addressing efficiency and substrate scope of such a process is presented. |
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Keywords: | Allylic alcohols Friedel-Crafts reaction Gold-catalysis Indole Stereoselection |
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