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...

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Autores principales: Sawicki, Marcin, Kwok, Angela, Tredwell, Matthew, Gouverneur, Véronique
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2007
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151074/
https://www.ncbi.nlm.nih.gov/pubmed/17961218
http://dx.doi.org/10.1186/1860-5397-3-34
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author Sawicki, Marcin
Kwok, Angela
Tredwell, Matthew
Gouverneur, Véronique
author_facet Sawicki, Marcin
Kwok, Angela
Tredwell, Matthew
Gouverneur, Véronique
author_sort Sawicki, Marcin
collection PubMed
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.
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spelling pubmed-21510742007-12-21 Single and double stereoselective fluorination of (E)-allylsilanes Sawicki, Marcin Kwok, Angela Tredwell, Matthew Gouverneur, Véronique Beilstein J Org Chem Preliminary Communication 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. Beilstein-Institut 2007-10-25 /pmc/articles/PMC2151074/ /pubmed/17961218 http://dx.doi.org/10.1186/1860-5397-3-34 Text en Copyright © 2007, Sawicki et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Sawicki, Marcin
Kwok, Angela
Tredwell, Matthew
Gouverneur, Véronique
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 Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151074/
https://www.ncbi.nlm.nih.gov/pubmed/17961218
http://dx.doi.org/10.1186/1860-5397-3-34
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AT tredwellmatthew singleanddoublestereoselectivefluorinationofeallylsilanes
AT gouverneurveronique singleanddoublestereoselectivefluorinationofeallylsilanes

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