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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...

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Autores principales: Schmid, Thibault E, Drissi-Amraoui, Sammy, Crévisy, Christophe, Baslé, Olivier, Mauduit, Marc
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
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.
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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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