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Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols
Herein we disclose an iron‐catalyzed cross‐coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri‐ and tetrasubstituted fluoroalkyl...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8518087/ https://www.ncbi.nlm.nih.gov/pubmed/34318557 http://dx.doi.org/10.1002/anie.202106742 |
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author | Posevins, Daniels Bermejo‐López, Aitor Bäckvall, Jan‐E. |
author_facet | Posevins, Daniels Bermejo‐López, Aitor Bäckvall, Jan‐E. |
author_sort | Posevins, Daniels |
collection | PubMed |
description | Herein we disclose an iron‐catalyzed cross‐coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri‐ and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron‐catalyzed cross‐coupling of Grignard reagents with α‐alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β‐ or γ‐allenols, respectively. |
format | Online Article Text |
id | pubmed-8518087 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-85180872021-10-21 Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols Posevins, Daniels Bermejo‐López, Aitor Bäckvall, Jan‐E. Angew Chem Int Ed Engl Communications Herein we disclose an iron‐catalyzed cross‐coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri‐ and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron‐catalyzed cross‐coupling of Grignard reagents with α‐alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β‐ or γ‐allenols, respectively. John Wiley and Sons Inc. 2021-09-02 2021-10-04 /pmc/articles/PMC8518087/ /pubmed/34318557 http://dx.doi.org/10.1002/anie.202106742 Text en © 2021 The Authors. Angewandte Chemie International Edition 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 Posevins, Daniels Bermejo‐López, Aitor Bäckvall, Jan‐E. Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols |
title | Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols |
title_full | Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols |
title_fullStr | Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols |
title_full_unstemmed | Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols |
title_short | Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols |
title_sort | iron‐catalyzed cross‐coupling of propargyl ethers with grignard reagents for the synthesis of functionalized allenes and allenols |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8518087/ https://www.ncbi.nlm.nih.gov/pubmed/34318557 http://dx.doi.org/10.1002/anie.202106742 |
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