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Single and double stereoselective fluorination of (E)-allylsilanes

Abstract:
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.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.1186/1860-5397-3-34

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Institution:
University of Oxford
Department:
Mathematical, Physical & Life Sciences Division - Chemistry - Chemistry Research Laboratory
More by this author
Institution:
University of Oxford
Department:
Mathematical, Physical & Life Sciences Division - Chemistry - Chemistry Research Laboratory
More by this author
Institution:
University of Oxford
Department:
Mathematical, Physical & Life Sciences Division - Chemistry - Chemistry Research Laboratory
More by this author
Institution:
University of Oxford
Oxford college:
Merton College
Department:
Mathematical, Physical & Life Sciences Division - Chemistry - Chemistry Research Laboratory

Contributors

Publisher:
Beilstein Institut Publisher's website
Journal:
Beilstein Journal of Organic Chemistry Journal website
Volume:
3
Pages:
Article: 34
Publication date:
2007-10-05
DOI:
URN:
uuid:4a8ea25b-5dee-4c50-b619-57c5d38b7a0a
Local pid:
ora:2773
Language:
English
Subjects:

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