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...
| Authors: | ; ; ; |
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| 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 |
| _version_ | 1878729550999846912 |
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| author | Altarejos Salido, Julia|||0000-0002-2871-8597 |
| author2 | Sucunza Sáenz, David|||0000-0002-3307-4204 Vaquero López, Juan José|||0000-0002-3820-9673 Carreras Pérez Aradros, Javier|||0000-0002-1521-6758 |
| author2_role | author author author |
| author_browse | Altarejos Salido, Julia|||0000-0002-2871-8597 Carreras Pérez Aradros, Javier|||0000-0002-1521-6758 Sucunza Sáenz, David|||0000-0002-3307-4204 Vaquero López, Juan José|||0000-0002-3820-9673 |
| author_facet | 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 |
| author_role | author |
| collection | e_Buah Biblioteca Digital Universidad de Alcalá |
| description | 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. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | ES_0a31fa351acd3f824ec8c8a13e2e00a7 |
| institution | Universidad de Alcalá (UAH) |
| instname_str | Universidad de Alcalá (UAH) |
| language | eng |
| network_acronym_str | ES |
| network_name_str | España |
| oai_identifier_str | oai:ebuah.uah.es:10017/49328 |
| publishDate | 2021 |
| publishDateSort | 2021 |
| reponame_str | e_Buah Biblioteca Digital Universidad de Alcalá |
| spelling | Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates 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 (Trifluoromethyl)cyclopropylboronates Enantioselective cyclopropanation Trifluorodiazoethane Alkenyl boronates Copper catalysis Trifluoromethylcyclopropanes Química Chemistry 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. Universidad de Alcalá Ministerio de Economía y Competitividad Ministerio de Ciencia e Innovación Comunidad de Madrid Agencia Estatal de Investigación http://hdl.handle.net/10017/49328 https://dx.doi.org/10.1021/acs.orglett.1c02420 |
| spellingShingle | Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates Altarejos Salido, Julia|||0000-0002-2871-8597 (Trifluoromethyl)cyclopropylboronates Enantioselective cyclopropanation Trifluorodiazoethane Alkenyl boronates Copper catalysis Trifluoromethylcyclopropanes Química Chemistry |
| 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 |
| topic | (Trifluoromethyl)cyclopropylboronates Enantioselective cyclopropanation Trifluorodiazoethane Alkenyl boronates Copper catalysis Trifluoromethylcyclopropanes Química Chemistry |
| topic_facet | (Trifluoromethyl)cyclopropylboronates Enantioselective cyclopropanation Trifluorodiazoethane Alkenyl boronates Copper catalysis Trifluoromethylcyclopropanes Química Chemistry |
| url | http://hdl.handle.net/10017/49328 https://dx.doi.org/10.1021/acs.orglett.1c02420 |