Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions
| Autor: | Fabien Gagosz, Olivier Riant, Marina Sanita, Arnaud Boreux, Dominic Campeau, Aubin Lambion, Ruben Coronel |
|---|---|
| Přispěvatelé: | Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de la matière condensée et des nanosciences / Institute of Condensed Matter and Nanosciences (IMCN), Université Catholique de Louvain = Catholic University of Louvain (UCL), Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry α Propargylic acetates Gold catalysis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Adduct Catalysis Trifluoromethyl group β-unsaturated ketones Drug Discovery Diels alder Organic chemistry Reactivity (chemistry) |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2018, 74 (38), pp.5232-5239. ⟨10.1016/j.tet.2018.05.054⟩ |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.05.054⟩ |
| Popis: | International audience; The synthesis of fluorinated synthetic intermediates has become a field of intense research in organic chemistry. In this article, we report the application of a gold-catalyzed rearrangement to the synthesis of β-trifluoromethylated α,β-unsaturated ketones. The scope of the reaction, as well as the valorization of the products in subsequent transformations has been investigated. This study allowed for the preparation of various CF3-substituted enones and fluorinated Diels-Alder adducts from easily accessible starting materials. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect