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Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines

Chiral indole derivatives are ubiquitous motifs in pharmaceuticals and alkaloids. Herein, the first protocol for catalytic asymmetric conjugate addition of Grignard reagents to various sulfonyl indoles, offering a straightforward approach for the synthesis of chiral 3‐sec‐alkyl‐substituted indoles i...

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Detalles Bibliográficos
Autores principales: Ge, Luo, Zurro, Mercedes, Harutyunyan, Syuzanna R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7918645/
https://www.ncbi.nlm.nih.gov/pubmed/32960461
http://dx.doi.org/10.1002/chem.202004232
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author Ge, Luo
Zurro, Mercedes
Harutyunyan, Syuzanna R.
author_facet Ge, Luo
Zurro, Mercedes
Harutyunyan, Syuzanna R.
author_sort Ge, Luo
collection PubMed
description Chiral indole derivatives are ubiquitous motifs in pharmaceuticals and alkaloids. Herein, the first protocol for catalytic asymmetric conjugate addition of Grignard reagents to various sulfonyl indoles, offering a straightforward approach for the synthesis of chiral 3‐sec‐alkyl‐substituted indoles in high yields and enantiomeric ratios is presented. This methodology makes use of a chiral catalyst based on copper phosphoramidite complexes and in situ formation of vinylogous imine intermediates.
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spelling pubmed-79186452021-03-11 Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines Ge, Luo Zurro, Mercedes Harutyunyan, Syuzanna R. Chemistry Communications Chiral indole derivatives are ubiquitous motifs in pharmaceuticals and alkaloids. Herein, the first protocol for catalytic asymmetric conjugate addition of Grignard reagents to various sulfonyl indoles, offering a straightforward approach for the synthesis of chiral 3‐sec‐alkyl‐substituted indoles in high yields and enantiomeric ratios is presented. This methodology makes use of a chiral catalyst based on copper phosphoramidite complexes and in situ formation of vinylogous imine intermediates. John Wiley and Sons Inc. 2020-11-09 2020-12-09 /pmc/articles/PMC7918645/ /pubmed/32960461 http://dx.doi.org/10.1002/chem.202004232 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Ge, Luo
Zurro, Mercedes
Harutyunyan, Syuzanna R.
Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
title Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
title_full Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
title_fullStr Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
title_full_unstemmed Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
title_short Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
title_sort copper‐catalyzed addition of grignard reagents to in situ generated indole‐derived vinylogous imines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7918645/
https://www.ncbi.nlm.nih.gov/pubmed/32960461
http://dx.doi.org/10.1002/chem.202004232
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