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Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides
An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8188512/ https://www.ncbi.nlm.nih.gov/pubmed/34168828 http://dx.doi.org/10.1039/d1sc00822f |
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author | DeLano, Travis J. Dibrell, Sara E. Lacker, Caitlin R. Pancoast, Adam R. Poremba, Kelsey E. Cleary, Leah Sigman, Matthew S. Reisman, Sarah E. |
author_facet | DeLano, Travis J. Dibrell, Sara E. Lacker, Caitlin R. Pancoast, Adam R. Poremba, Kelsey E. Cleary, Leah Sigman, Matthew S. Reisman, Sarah E. |
author_sort | DeLano, Travis J. |
collection | PubMed |
description | An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity. |
format | Online Article Text |
id | pubmed-8188512 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81885122021-06-23 Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides DeLano, Travis J. Dibrell, Sara E. Lacker, Caitlin R. Pancoast, Adam R. Poremba, Kelsey E. Cleary, Leah Sigman, Matthew S. Reisman, Sarah E. Chem Sci Chemistry An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity. The Royal Society of Chemistry 2021-04-26 /pmc/articles/PMC8188512/ /pubmed/34168828 http://dx.doi.org/10.1039/d1sc00822f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry DeLano, Travis J. Dibrell, Sara E. Lacker, Caitlin R. Pancoast, Adam R. Poremba, Kelsey E. Cleary, Leah Sigman, Matthew S. Reisman, Sarah E. Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
title | Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
title_full | Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
title_fullStr | Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
title_full_unstemmed | Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
title_short | Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
title_sort | nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8188512/ https://www.ncbi.nlm.nih.gov/pubmed/34168828 http://dx.doi.org/10.1039/d1sc00822f |
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