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Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ethers based on the use of vinylbenziodoxolo...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6430016/ https://www.ncbi.nlm.nih.gov/pubmed/30996905 http://dx.doi.org/10.1039/c8sc05573d |
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author | Caramenti, Paola Declas, Nina Tessier, Romain Wodrich, Matthew D. Waser, Jerome |
author_facet | Caramenti, Paola Declas, Nina Tessier, Romain Wodrich, Matthew D. Waser, Jerome |
author_sort | Caramenti, Paola |
collection | PubMed |
description | Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ethers based on the use of vinylbenziodoxolone (VBX) reagents. The stable VBX reagents were synthesized by stereoselective addition of N- or O-nucleophiles on the corresponding alkynyl reagents in the presence of a catalytic amount of cesium carbonate. The VBX reagents were used in palladium-catalyzed cross-couplings at room temperature to access Z-enamides and enol ethers. |
format | Online Article Text |
id | pubmed-6430016 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-64300162019-04-17 Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers Caramenti, Paola Declas, Nina Tessier, Romain Wodrich, Matthew D. Waser, Jerome Chem Sci Chemistry Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ethers based on the use of vinylbenziodoxolone (VBX) reagents. The stable VBX reagents were synthesized by stereoselective addition of N- or O-nucleophiles on the corresponding alkynyl reagents in the presence of a catalytic amount of cesium carbonate. The VBX reagents were used in palladium-catalyzed cross-couplings at room temperature to access Z-enamides and enol ethers. Royal Society of Chemistry 2019-02-04 /pmc/articles/PMC6430016/ /pubmed/30996905 http://dx.doi.org/10.1039/c8sc05573d Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Caramenti, Paola Declas, Nina Tessier, Romain Wodrich, Matthew D. Waser, Jerome Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers |
title | Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
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title_full | Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
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title_fullStr | Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
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title_full_unstemmed | Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
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title_short | Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
|
title_sort | stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted z-enamides and enol ethers |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6430016/ https://www.ncbi.nlm.nih.gov/pubmed/30996905 http://dx.doi.org/10.1039/c8sc05573d |
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