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Single and double stereoselective fluorination of (E)-allylsilanes

Sawicki, Marcin, Kwok, Angela, Tredwell, Matthew ORCID: and Gouverneur, Veronique 2007. Single and double stereoselective fluorination of (E)-allylsilanes. Beilstein Journal of Organic Chemistry 3 (1) , p. 34. 10.1186/1860-5397-3-34

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Acyclic allylic monofluorides were prepared by electrophilic fluorination of branched (E)-allylsilanes with Selectfluor. These reactions proceeded with efficient transfer of chirality from the silylated to the fluorinated stereocentre. Upon double fluorination, an unsymmetrical ethyl syn-2,5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an anti stereodirecting group for the two C-F bond forming events.

Item Type: Article
Status: Published
Schools: Medicine
Publisher: Beilstein-Institut
ISSN: 1860-5397
Last Modified: 04 Nov 2022 12:12

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