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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...

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Autores principales: DeLano, Travis J., Dibrell, Sara E., Lacker, Caitlin R., Pancoast, Adam R., Poremba, Kelsey E., Cleary, Leah, Sigman, Matthew S., Reisman, Sarah E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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.
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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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