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 <em>syn&l...
| Auteurs principaux: | , , , |
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| Format: | Journal article |
| Langue: | English |
| Publié: |
Beilstein Institut
2007
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| Sujets: |
| _version_ | 1826270948745019392 |
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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 <em>syn</em>-2.5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an <em>anti</em> stereodirecting group for the two C-F bond forming events. |
| first_indexed | 2024-03-06T21:48:53Z |
| format | Journal article |
| id | oxford-uuid:4a8ea25b-5dee-4c50-b619-57c5d38b7a0a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:48:53Z |
| publishDate | 2007 |
| publisher | Beilstein Institut |
| record_format | dspace |
| spelling | oxford-uuid:4a8ea25b-5dee-4c50-b619-57c5d38b7a0a2022-03-26T15:38:19ZSingle and double stereoselective fluorination of (E)-allylsilanesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:4a8ea25b-5dee-4c50-b619-57c5d38b7a0aChemistry & allied sciencesEnglishOxford University Research Archive - ValetBeilstein Institut2007Sawicki, 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 <em>syn</em>-2.5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an <em>anti</em> stereodirecting group for the two C-F bond forming events. |
| spellingShingle | Chemistry & allied sciences 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 |
| topic | Chemistry & allied sciences |
| work_keys_str_mv | AT sawickim singleanddoublestereoselectivefluorinationofeallylsilanes AT kwoka singleanddoublestereoselectivefluorinationofeallylsilanes AT tredwellm singleanddoublestereoselectivefluorinationofeallylsilanes AT gouverneurv singleanddoublestereoselectivefluorinationofeallylsilanes |