Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates

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 valuab...

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Bibliographic Details
Authors: Altarejos Salido, Julia|||0000-0002-2871-8597, Sucunza Sáenz, David|||0000-0002-3307-4204, Vaquero López, Juan José|||0000-0002-3820-9673, Carreras Pérez Aradros, Javier|||0000-0002-1521-6758
Format: article
Publication Date:2021
Country:España
Institution:Universidad de Alcalá (UAH)
Repository:e_Buah Biblioteca Digital Universidad de Alcalá
Language:English
OAI Identifier:oai:ebuah.uah.es:10017/49328
Online Access:http://hdl.handle.net/10017/49328
https://dx.doi.org/10.1021/acs.orglett.1c02420
Access Level:Open access
Keyword:(Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Química
Chemistry
Description
Summary: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.