Asymmetric organocatalytic monofluorovinylations |
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Authors: | Jacobsen Christian Borch Nielsen Martin Worgull Dennis Zweifel Theo Fisker Esben Jørgensen Karl Anker |
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Affiliation: | Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark. |
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Abstract: | The development of highly enantio- and diastereoselective organocatalytic monofluorovinylations is presented. Based on the application of α-fluoro-β-keto-benzothiazolesulfones, the formal addition of a monofluorovinylic anion synthon to a range of acyclic and cyclic enones, as well as imines, is shown. These procedures give selective access to both E- and Z-isomers of the monofluorovinylated products, which are isolated as the pure diastereoisomers in good to excellent yields with up to 99% ee. Furthermore, the application of this concept for the formation of highly enantioenriched bicylic compounds containing a monofluorovinyl moiety is also described. In addition, a mechanistic rationale for the observed E:Z-selectivities is presented. |
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