Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles

A copper‐catalyzed conjugate silylation of various cyclobutenone derivatives with Me(2)PhSiZnCl ⋅ 2LiCl or (Me(2)PhSi)(2)Zn ⋅ xLiCl (x≤4) to generate β‐silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh)(2) affords silylated enol phosphates that can be further en...

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Autores principales: Cui, Ming, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9292915/
https://www.ncbi.nlm.nih.gov/pubmed/34490934
http://dx.doi.org/10.1002/chem.202102993
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author Cui, Ming
Oestreich, Martin
author_facet Cui, Ming
Oestreich, Martin
author_sort Cui, Ming
collection PubMed
description A copper‐catalyzed conjugate silylation of various cyclobutenone derivatives with Me(2)PhSiZnCl ⋅ 2LiCl or (Me(2)PhSi)(2)Zn ⋅ xLiCl (x≤4) to generate β‐silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh)(2) affords silylated enol phosphates that can be further engaged in Kumada cross‐coupling reactions to yield silylated cyclobutene derivatives.
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spelling pubmed-92929152022-07-20 Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles Cui, Ming Oestreich, Martin Chemistry Communications A copper‐catalyzed conjugate silylation of various cyclobutenone derivatives with Me(2)PhSiZnCl ⋅ 2LiCl or (Me(2)PhSi)(2)Zn ⋅ xLiCl (x≤4) to generate β‐silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh)(2) affords silylated enol phosphates that can be further engaged in Kumada cross‐coupling reactions to yield silylated cyclobutene derivatives. John Wiley and Sons Inc. 2021-10-07 2021-11-22 /pmc/articles/PMC9292915/ /pubmed/34490934 http://dx.doi.org/10.1002/chem.202102993 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Cui, Ming
Oestreich, Martin
Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
title Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
title_full Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
title_fullStr Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
title_full_unstemmed Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
title_short Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4‐Addition of Zinc‐Based Silicon Nucleophiles
title_sort synthesis of silylated cyclobutanone and cyclobutene derivatives involving 1,4‐addition of zinc‐based silicon nucleophiles
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9292915/
https://www.ncbi.nlm.nih.gov/pubmed/34490934
http://dx.doi.org/10.1002/chem.202102993
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