An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols

[Image: see text] An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates...

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Autores principales: Zi, Weiwei, Wang, Yi-Ming, Toste, F. Dean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183625/
https://www.ncbi.nlm.nih.gov/pubmed/25203796
http://dx.doi.org/10.1021/ja507468u
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author Zi, Weiwei
Wang, Yi-Ming
Toste, F. Dean
author_facet Zi, Weiwei
Wang, Yi-Ming
Toste, F. Dean
author_sort Zi, Weiwei
collection PubMed
description [Image: see text] An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates underwent fluorination to afford highly enantioenriched α-fluoro homoallylic alcohols. Mechanistic studies suggest that this transformation proceeds through a concerted enantiodetermining transition state involving both C–F bond formation and C–H bond cleavage.
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spelling pubmed-41836252015-09-09 An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols Zi, Weiwei Wang, Yi-Ming Toste, F. Dean J Am Chem Soc [Image: see text] An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates underwent fluorination to afford highly enantioenriched α-fluoro homoallylic alcohols. Mechanistic studies suggest that this transformation proceeds through a concerted enantiodetermining transition state involving both C–F bond formation and C–H bond cleavage. American Chemical Society 2014-09-09 2014-09-17 /pmc/articles/PMC4183625/ /pubmed/25203796 http://dx.doi.org/10.1021/ja507468u Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Zi, Weiwei
Wang, Yi-Ming
Toste, F. Dean
An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols
title An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols
title_full An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols
title_fullStr An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols
title_full_unstemmed An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols
title_short An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols
title_sort in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183625/
https://www.ncbi.nlm.nih.gov/pubmed/25203796
http://dx.doi.org/10.1021/ja507468u
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