Asymmetric Organocatalytic Monofluorovinylations

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 sho...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-05, Vol.133 (19), p.7398-7404
Main Authors: Jacobsen, Christian Borch, Nielsen, Martin, Worgull, Dennis, Zweifel, Theo, Fisker, Esben, Jørgensen, Karl Anker
Format: Article
Language:English
Subjects:
Catalysis
Fluorine - chemistry
Molecular Structure
Peptides - chemistry
Stereoisomerism
Sulfones - chemistry
Thiazoles - chemistry
Vinyl Compounds - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja110624k