Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation
Main Author: | |
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Publication Date: | 2014 |
Other Authors: | , , |
Format: | Article |
Language: | por |
Source: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Download full: | http://hdl.handle.net/10174/13455 https://doi.org/10.1002/ejoc.201403180 |
Summary: | Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosilane to imines. Excellent yields with good to high enantioselectivities (up to 91%) were obtained in the reduction of differently substituted substrates. Noteworthy, remarkably high turnover frequencies for the hydrosilylation of imines were observed; the catalyst of choice proved to be active even at a loading of only 1 mol-%. The loading was further reduced to 0.5 mol-%, and for very short reaction times (15 min) very impressive asymmetric catalyst efficiency speed values were reached. |
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Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine HydrosilylationOrganocatáliseHidrosililaçãoPicolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosilane to imines. Excellent yields with good to high enantioselectivities (up to 91%) were obtained in the reduction of differently substituted substrates. Noteworthy, remarkably high turnover frequencies for the hydrosilylation of imines were observed; the catalyst of choice proved to be active even at a loading of only 1 mol-%. The loading was further reduced to 0.5 mol-%, and for very short reaction times (15 min) very impressive asymmetric catalyst efficiency speed values were reached.Wiley-VCH2015-03-20T15:08:13Z2015-03-202014-11-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10174/13455http://hdl.handle.net/10174/13455https://doi.org/10.1002/ejoc.201403180por7339-73421434-193X33European Journal Organic Chemistryajb@uevora.ptpbarrulas@uevora.ptmaurizio.benaglia@unimi.itandrea.genoni@unimi.itCinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation307Burke, AnthonyBarrulas, PedroBenaglia, MaurizioAndrea, Genoniinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-01-03T18:58:55Zoai:dspace.uevora.pt:10174/13455Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:06:53.952349Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
title |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
spellingShingle |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation Burke, Anthony Organocatálise Hidrosililação |
title_short |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
title_full |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
title_fullStr |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
title_full_unstemmed |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
title_sort |
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation |
author |
Burke, Anthony |
author_facet |
Burke, Anthony Barrulas, Pedro Benaglia, Maurizio Andrea, Genoni |
author_role |
author |
author2 |
Barrulas, Pedro Benaglia, Maurizio Andrea, Genoni |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Burke, Anthony Barrulas, Pedro Benaglia, Maurizio Andrea, Genoni |
dc.subject.por.fl_str_mv |
Organocatálise Hidrosililação |
topic |
Organocatálise Hidrosililação |
description |
Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosilane to imines. Excellent yields with good to high enantioselectivities (up to 91%) were obtained in the reduction of differently substituted substrates. Noteworthy, remarkably high turnover frequencies for the hydrosilylation of imines were observed; the catalyst of choice proved to be active even at a loading of only 1 mol-%. The loading was further reduced to 0.5 mol-%, and for very short reaction times (15 min) very impressive asymmetric catalyst efficiency speed values were reached. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-11-01T00:00:00Z 2015-03-20T15:08:13Z 2015-03-20 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10174/13455 http://hdl.handle.net/10174/13455 https://doi.org/10.1002/ejoc.201403180 |
url |
http://hdl.handle.net/10174/13455 https://doi.org/10.1002/ejoc.201403180 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.none.fl_str_mv |
7339-7342 1434-193X 33 European Journal Organic Chemistry ajb@uevora.pt pbarrulas@uevora.pt maurizio.benaglia@unimi.it andrea.genoni@unimi.it Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation 307 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Wiley-VCH |
publisher.none.fl_str_mv |
Wiley-VCH |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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