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Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors
The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic ce...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685790/ https://www.ncbi.nlm.nih.gov/pubmed/26734090 http://dx.doi.org/10.3762/bjoc.11.263 |
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author | Schmid, Thibault E Drissi-Amraoui, Sammy Crévisy, Christophe Baslé, Olivier Mauduit, Marc |
author_facet | Schmid, Thibault E Drissi-Amraoui, Sammy Crévisy, Christophe Baslé, Olivier Mauduit, Marc |
author_sort | Schmid, Thibault E |
collection | PubMed |
description | The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic centers. In the last decade, various chiral copper-based catalysts were evaluated in combination with different nucleophiles and Michael acceptors, and have unambiguously demonstrated their usefulness in the control of the regio- and enantioselectivity of the addition. The aim of this review is to report recent breakthroughs achieved in this challenging field. |
format | Online Article Text |
id | pubmed-4685790 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-46857902016-01-05 Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors Schmid, Thibault E Drissi-Amraoui, Sammy Crévisy, Christophe Baslé, Olivier Mauduit, Marc Beilstein J Org Chem Review The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic centers. In the last decade, various chiral copper-based catalysts were evaluated in combination with different nucleophiles and Michael acceptors, and have unambiguously demonstrated their usefulness in the control of the regio- and enantioselectivity of the addition. The aim of this review is to report recent breakthroughs achieved in this challenging field. Beilstein-Institut 2015-12-03 /pmc/articles/PMC4685790/ /pubmed/26734090 http://dx.doi.org/10.3762/bjoc.11.263 Text en Copyright © 2015, Schmid et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Review Schmid, Thibault E Drissi-Amraoui, Sammy Crévisy, Christophe Baslé, Olivier Mauduit, Marc Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors |
title | Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors |
title_full | Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors |
title_fullStr | Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors |
title_full_unstemmed | Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors |
title_short | Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors |
title_sort | copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended michael acceptors |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685790/ https://www.ncbi.nlm.nih.gov/pubmed/26734090 http://dx.doi.org/10.3762/bjoc.11.263 |
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