1296831-95-2Relevant academic research and scientific papers
Asymmetric organocatalytic monofluorovinylations
Jacobsen, Christian Borch,Nielsen, Martin,Worgull, Dennis,Zweifel, Theo,Fisker, Esben,Jorgensen, Karl Anker
, p. 7398 - 7404 (2011/06/24)
The development of highly enantio-and diastereoselective organocatalytic monofluorovinylations is presented. Based on the application of β-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.
