Single and double stereoselective fluorination of (E)-allylsilanes.
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-difluor...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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2007
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| _version_ | 1797086811762196480 |
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| author | Sawicki, M Kwok, A Tredwell, M Gouverneur, V |
| author_facet | Sawicki, M Kwok, A Tredwell, M Gouverneur, V |
| author_sort | Sawicki, M |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-07T02:27:17Z |
| format | Journal article |
| id | oxford-uuid:a60c72cf-832a-4533-9ccd-7ad285078d81 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:27:17Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:a60c72cf-832a-4533-9ccd-7ad285078d812022-03-27T02:44:31ZSingle and double stereoselective fluorination of (E)-allylsilanes.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:a60c72cf-832a-4533-9ccd-7ad285078d81EnglishSymplectic Elements at Oxford2007Sawicki, MKwok, ATredwell, MGouverneur, VAcyclic 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. |
| spellingShingle | Sawicki, M Kwok, A Tredwell, M Gouverneur, V Single and double stereoselective fluorination of (E)-allylsilanes. |
| title | Single and double stereoselective fluorination of (E)-allylsilanes. |
| title_full | Single and double stereoselective fluorination of (E)-allylsilanes. |
| title_fullStr | Single and double stereoselective fluorination of (E)-allylsilanes. |
| title_full_unstemmed | Single and double stereoselective fluorination of (E)-allylsilanes. |
| title_short | Single and double stereoselective fluorination of (E)-allylsilanes. |
| title_sort | single and double stereoselective fluorination of e allylsilanes |
| work_keys_str_mv | AT sawickim singleanddoublestereoselectivefluorinationofeallylsilanes AT kwoka singleanddoublestereoselectivefluorinationofeallylsilanes AT tredwellm singleanddoublestereoselectivefluorinationofeallylsilanes AT gouverneurv singleanddoublestereoselectivefluorinationofeallylsilanes |