Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids

[Image: see text] A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diast...

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Autores principales: Bandar, Jeffrey S., Ascic, Erhad, Buchwald, Stephen L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4866599/
https://www.ncbi.nlm.nih.gov/pubmed/27121395
http://dx.doi.org/10.1021/jacs.6b03086
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author Bandar, Jeffrey S.
Ascic, Erhad
Buchwald, Stephen L.
author_facet Bandar, Jeffrey S.
Ascic, Erhad
Buchwald, Stephen L.
author_sort Bandar, Jeffrey S.
collection PubMed
description [Image: see text] A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.
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spelling pubmed-48665992017-04-27 Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids Bandar, Jeffrey S. Ascic, Erhad Buchwald, Stephen L. J Am Chem Soc [Image: see text] A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance. American Chemical Society 2016-04-27 2016-05-11 /pmc/articles/PMC4866599/ /pubmed/27121395 http://dx.doi.org/10.1021/jacs.6b03086 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Bandar, Jeffrey S.
Ascic, Erhad
Buchwald, Stephen L.
Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
title Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
title_full Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
title_fullStr Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
title_full_unstemmed Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
title_short Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
title_sort enantioselective cuh-catalyzed reductive coupling of aryl alkenes and activated carboxylic acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4866599/
https://www.ncbi.nlm.nih.gov/pubmed/27121395
http://dx.doi.org/10.1021/jacs.6b03086
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AT ascicerhad enantioselectivecuhcatalyzedreductivecouplingofarylalkenesandactivatedcarboxylicacids
AT buchwaldstephenl enantioselectivecuhcatalyzedreductivecouplingofarylalkenesandactivatedcarboxylicacids

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