Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates

Authors
Altarejos Salido, JuliaUniversity of Alcalá Author; Sucunza Sáenz, DavidUniversity of Alcalá Author; Vaquero López, Juan J.; Carreras Pérez Aradros, JavierUniversity of Alcalá Author
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/49328
DOI: 10.1021/acs.orglett.1c02420
ISSN: 1523-7060
Date
2021-07-28
Embargo end date
2022-07-28
Affiliation
Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica
Bibliographic citation
Organic Letters, 2021, v. 23, n. 15, p. 6174-6178
Keywords
(Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Project
PID2019-105007GAI00 (Ministerio de Ciencia e Innovación); CTQ2017-85263-R (MINECO); RD16/0009/0015 (RETIC REDinREN, Instituto de Salud Carlos III); CM/JIN/2019-025 (Comunidad de Madrid y Universidad de Alcalá); CCG19/CC-038 (Universidad de Alcalá)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© 2021 American Chemical Society
Access rights
info:eu-repo/semantics/openAccess
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Abstract
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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