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Gold(I)‐Assisted α‐Allylation of Enals and Enones with Alcohols |
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| Authors: | Marco Michele Mastandrea Niall Mellonie Pietro Giacinto Dr Alba Collado Prof Dr Steven P Nolan Dr Gian Pietro Miscione Prof Andrea Bottoni Prof Marco Bandini |
| Affiliation: | 1. Department of Chemistry “G. Ciamician”, Alma Mater Studiorum—University of Bologna, via Selmi 2, 40126, Bologna (Italy);2. EaStCHEM School of Chemistry, University of St. Andrews, St. Andrews, KY16 9ST (UK);3. Chemistry Department, College of Science, King Saud University, Riyadh 11451 (Saudi Arabia);4. Department of Chemistry, Universidad de los Andes, Carrera 1 N° 18A 10, Bogotá (Colombia) |
| Abstract: | The intermolecular α‐allylation of enals and enones occurs by the condensation of variously substituted allenamides with allylic alcohols. Cooperative catalysis by Au(ItBu)NTf2] and AgNTf2 enables the synthesis of a range of densely functionalized α‐allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an α‐gold(I) enal/enone as the active nucleophilic species. |
| Keywords: | alcohols allylation gold catalysis reaction mechanisms unsaturated carbonyl compounds |
