Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**

Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94 % ee) or α-chloroesters (up to 94 % ee). Either 2-arylsubstit...

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Detalles Bibliográficos
Autores principales: Douglas, James J, Churchill, Gwydion, Slawin, Alexandra M Z, Fox, David J, Smith, Andrew D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648049/
https://www.ncbi.nlm.nih.gov/pubmed/26406613
http://dx.doi.org/10.1002/chem.201503308
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author Douglas, James J
Churchill, Gwydion
Slawin, Alexandra M Z
Fox, David J
Smith, Andrew D
author_facet Douglas, James J
Churchill, Gwydion
Slawin, Alexandra M Z
Fox, David J
Smith, Andrew D
author_sort Douglas, James J
collection PubMed
description Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94 % ee) or α-chloroesters (up to 94 % ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.
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spelling pubmed-46480492015-11-24 Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral** Douglas, James J Churchill, Gwydion Slawin, Alexandra M Z Fox, David J Smith, Andrew D Chemistry Communications Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94 % ee) or α-chloroesters (up to 94 % ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis. WILEY-VCH Verlag 2015-11-09 2015-09-25 /pmc/articles/PMC4648049/ /pubmed/26406613 http://dx.doi.org/10.1002/chem.201503308 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co.KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reprodu.ction in anymedium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co.KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reprodu.ction in anymedium, provided the original work is properly cited.
spellingShingle Communications
Douglas, James J
Churchill, Gwydion
Slawin, Alexandra M Z
Fox, David J
Smith, Andrew D
Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**
title Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**
title_full Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**
title_fullStr Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**
title_full_unstemmed Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**
title_short Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral**
title_sort stereo- and chemodivergent nhc-promoted functionalisation of arylalkylketenes with chloral**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648049/
https://www.ncbi.nlm.nih.gov/pubmed/26406613
http://dx.doi.org/10.1002/chem.201503308
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