Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Posevins, Daniels, Bermejo‐López, Aitor, Bäckvall, Jan‐E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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
_version_ 1784584148699054080
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
work_keys_str_mv AT posevinsdaniels ironcatalyzedcrosscouplingofpropargyletherswithgrignardreagentsforthesynthesisoffunctionalizedallenesandallenols
AT bermejolopezaitor ironcatalyzedcrosscouplingofpropargyletherswithgrignardreagentsforthesynthesisoffunctionalizedallenesandallenols
AT backvalljane ironcatalyzedcrosscouplingofpropargyletherswithgrignardreagentsforthesynthesisoffunctionalizedallenesandallenols