α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers

[Image: see text] A methodology for the construction of sterically congested quaternary centers via the trapping of vinyl carbocations with silyl ketene acetals is disclosed. This main group-catalyzed α-vinylation reaction is advantageous as methods to access these congested motifs are limited. More...

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Autores principales: Williams, Chloe G., Nistanaki, Sepand K., Wells, Conner W., Nelson, Hosea M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10226172/
https://www.ncbi.nlm.nih.gov/pubmed/37192420
http://dx.doi.org/10.1021/acs.orglett.3c00535
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author Williams, Chloe G.
Nistanaki, Sepand K.
Wells, Conner W.
Nelson, Hosea M.
author_facet Williams, Chloe G.
Nistanaki, Sepand K.
Wells, Conner W.
Nelson, Hosea M.
author_sort Williams, Chloe G.
collection PubMed
description [Image: see text] A methodology for the construction of sterically congested quaternary centers via the trapping of vinyl carbocations with silyl ketene acetals is disclosed. This main group-catalyzed α-vinylation reaction is advantageous as methods to access these congested motifs are limited. Moreover, β,γ-unsaturated carbonyl moieties and tetrasubstituted alkenes are present in various bioactive natural products and pharmaceuticals, and this catalytic platform offers a means of accessing them using simple and inexpensive materials.
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spelling pubmed-102261722023-05-30 α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers Williams, Chloe G. Nistanaki, Sepand K. Wells, Conner W. Nelson, Hosea M. Org Lett [Image: see text] A methodology for the construction of sterically congested quaternary centers via the trapping of vinyl carbocations with silyl ketene acetals is disclosed. This main group-catalyzed α-vinylation reaction is advantageous as methods to access these congested motifs are limited. Moreover, β,γ-unsaturated carbonyl moieties and tetrasubstituted alkenes are present in various bioactive natural products and pharmaceuticals, and this catalytic platform offers a means of accessing them using simple and inexpensive materials. American Chemical Society 2023-05-16 /pmc/articles/PMC10226172/ /pubmed/37192420 http://dx.doi.org/10.1021/acs.orglett.3c00535 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Williams, Chloe G.
Nistanaki, Sepand K.
Wells, Conner W.
Nelson, Hosea M.
α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers
title α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers
title_full α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers
title_fullStr α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers
title_full_unstemmed α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers
title_short α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers
title_sort α-vinylation of ester equivalents via main group catalysis for the construction of quaternary centers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10226172/
https://www.ncbi.nlm.nih.gov/pubmed/37192420
http://dx.doi.org/10.1021/acs.orglett.3c00535
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AT wellsconnerw avinylationofesterequivalentsviamaingroupcatalysisfortheconstructionofquaternarycenters
AT nelsonhoseam avinylationofesterequivalentsviamaingroupcatalysisfortheconstructionofquaternarycenters

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