Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates

[Image: see text] A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The p...

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Autores principales: Altarejos, Julia, Sucunza, David, Vaquero, Juan J., Carreras, Javier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8895459/
https://www.ncbi.nlm.nih.gov/pubmed/34320310
http://dx.doi.org/10.1021/acs.orglett.1c02420
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author Altarejos, Julia
Sucunza, David
Vaquero, Juan J.
Carreras, Javier
author_facet Altarejos, Julia
Sucunza, David
Vaquero, Juan J.
Carreras, Javier
author_sort Altarejos, Julia
collection PubMed
description [Image: see text] A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuable synthetic intermediates by transformation of the boronate group. This methodology can be applied to the synthesis of novel trifluoromethylated analogues of trans-2-arylcyclopropylamines, which are prevalent motifs in biologically active compounds.
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spelling pubmed-88954592022-03-07 Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates Altarejos, Julia Sucunza, David Vaquero, Juan J. Carreras, Javier Org Lett [Image: see text] A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuable synthetic intermediates by transformation of the boronate group. This methodology can be applied to the synthesis of novel trifluoromethylated analogues of trans-2-arylcyclopropylamines, which are prevalent motifs in biologically active compounds. American Chemical Society 2021-07-28 2021-08-06 /pmc/articles/PMC8895459/ /pubmed/34320310 http://dx.doi.org/10.1021/acs.orglett.1c02420 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Altarejos, Julia
Sucunza, David
Vaquero, Juan J.
Carreras, Javier
Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_full Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_fullStr Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_full_unstemmed Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_short Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_sort enantioselective copper-catalyzed synthesis of trifluoromethyl-cyclopropylboronates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8895459/
https://www.ncbi.nlm.nih.gov/pubmed/34320310
http://dx.doi.org/10.1021/acs.orglett.1c02420
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AT vaquerojuanj enantioselectivecoppercatalyzedsynthesisoftrifluoromethylcyclopropylboronates
AT carrerasjavier enantioselectivecoppercatalyzedsynthesisoftrifluoromethylcyclopropylboronates

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