Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2013 |
| Outros Autores: | , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UNIFESP |
| Texto Completo: | http://dx.doi.org/10.5935/0103-5053.20130181 http://repositorio.unifesp.br/handle/11600/7957 |
Resumo: | The kinetic resolutions of (±)-β-azidophenylethanols were carried out using lipase from Candida antarctica, and enantiomerically enriched (R)-β-azidophenylethanols and their corresponding (S)-β-azidophenylethyl acetates were obtained in good enantiomeric excesses (up to > 99%). The enantiomerically enriched (R)-β-azidophenylethanols were subjected to cyclization reaction with 2-(trimethylsilyl)phenyl triflate and CsF producing chiral 1,2,3-benzotriazole compounds in good yields (75-86%) by a [3 + 2] cycloaddition, which involves the benzyne formation. |
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Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazolesCALBlipasebiocatalysisclick chemistry[3 + 2]cycloadditionThe kinetic resolutions of (±)-β-azidophenylethanols were carried out using lipase from Candida antarctica, and enantiomerically enriched (R)-β-azidophenylethanols and their corresponding (S)-β-azidophenylethyl acetates were obtained in good enantiomeric excesses (up to > 99%). The enantiomerically enriched (R)-β-azidophenylethanols were subjected to cyclization reaction with 2-(trimethylsilyl)phenyl triflate and CsF producing chiral 1,2,3-benzotriazole compounds in good yields (75-86%) by a [3 + 2] cycloaddition, which involves the benzyne formation.As resoluções cinéticas de (±)-β-azidofeniletanóis foram realizadas usando a lipase de Candida antarctica fornecendo os compostos enantiomericamente enriquecidos, (R)-β-azidofeniletanóis e acetato de (S)-β-azidofeniletila em bons excessos enantioméricos (até > 99%). Os (R)-β-azidofeniletanóis enantiomericamente enriquecidos foram submetidos à reação de ciclização com o triflato de 2-(trimetilsilil)fenila e CsF resultando em 1,2,3-benzotriazóis em bons rendimentos (75-86%) pela reação de cicloadição [3 + 2], a qual envolve a formação in situ de benzino.Universidade de São Paulo Instituto de Química de São CarlosUniversidade Federal de São Paulo (UNIFESP) Departamento de Ciências Exatas e da TerraUniversidade Estadual de Mato Grosso do Sul Coordenação de QuímicaUNIFESP, Depto. de Ciências Exatas e da TerraSciELOFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Sociedade Brasileira de QuímicaUniversidade de São Paulo (USP)Universidade Federal de São Paulo (UNIFESP)Universidade Estadual de Mato Grosso do Sul Coordenação de QuímicaRocha, Lenilson CoutinhoRosset, Isac GeorgeMelgar, Gliseida ZelayaranRaminelli, Cristiano [UNIFESP]Porto, André Luiz MeleiroJeller, Alex Haroldo2015-06-14T13:45:37Z2015-06-14T13:45:37Z2013-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion1427-1432application/pdfhttp://dx.doi.org/10.5935/0103-5053.20130181Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 24, n. 9, p. 1427-1432, 2013.10.5935/0103-5053.20130181S0103-50532013000900006.pdf0103-50531678-4790S0103-50532013000900006http://repositorio.unifesp.br/handle/11600/7957WOS:000324933300006engJournal of the Brazilian Chemical Societyinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-07-29T02:08:12Zoai:repositorio.unifesp.br/:11600/7957Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-07-29T02:08:12Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false |
| dc.title.none.fl_str_mv |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| title |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| spellingShingle |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles Rocha, Lenilson Coutinho CALB lipase biocatalysis click chemistry [3 + 2] cycloaddition |
| title_short |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| title_full |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| title_fullStr |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| title_full_unstemmed |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| title_sort |
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles |
| author |
Rocha, Lenilson Coutinho |
| author_facet |
Rocha, Lenilson Coutinho Rosset, Isac George Melgar, Gliseida Zelayaran Raminelli, Cristiano [UNIFESP] Porto, André Luiz Meleiro Jeller, Alex Haroldo |
| author_role |
author |
| author2 |
Rosset, Isac George Melgar, Gliseida Zelayaran Raminelli, Cristiano [UNIFESP] Porto, André Luiz Meleiro Jeller, Alex Haroldo |
| author2_role |
author author author author author |
| dc.contributor.none.fl_str_mv |
Universidade de São Paulo (USP) Universidade Federal de São Paulo (UNIFESP) Universidade Estadual de Mato Grosso do Sul Coordenação de Química |
| dc.contributor.author.fl_str_mv |
Rocha, Lenilson Coutinho Rosset, Isac George Melgar, Gliseida Zelayaran Raminelli, Cristiano [UNIFESP] Porto, André Luiz Meleiro Jeller, Alex Haroldo |
| dc.subject.por.fl_str_mv |
CALB lipase biocatalysis click chemistry [3 + 2] cycloaddition |
| topic |
CALB lipase biocatalysis click chemistry [3 + 2] cycloaddition |
| description |
The kinetic resolutions of (±)-β-azidophenylethanols were carried out using lipase from Candida antarctica, and enantiomerically enriched (R)-β-azidophenylethanols and their corresponding (S)-β-azidophenylethyl acetates were obtained in good enantiomeric excesses (up to > 99%). The enantiomerically enriched (R)-β-azidophenylethanols were subjected to cyclization reaction with 2-(trimethylsilyl)phenyl triflate and CsF producing chiral 1,2,3-benzotriazole compounds in good yields (75-86%) by a [3 + 2] cycloaddition, which involves the benzyne formation. |
| publishDate |
2013 |
| dc.date.none.fl_str_mv |
2013-09-01 2015-06-14T13:45:37Z 2015-06-14T13:45:37Z |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.5935/0103-5053.20130181 Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 24, n. 9, p. 1427-1432, 2013. 10.5935/0103-5053.20130181 S0103-50532013000900006.pdf 0103-5053 1678-4790 S0103-50532013000900006 http://repositorio.unifesp.br/handle/11600/7957 WOS:000324933300006 |
| url |
http://dx.doi.org/10.5935/0103-5053.20130181 http://repositorio.unifesp.br/handle/11600/7957 |
| identifier_str_mv |
Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 24, n. 9, p. 1427-1432, 2013. 10.5935/0103-5053.20130181 S0103-50532013000900006.pdf 0103-5053 1678-4790 S0103-50532013000900006 WOS:000324933300006 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
Journal of the Brazilian Chemical Society |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
| dc.format.none.fl_str_mv |
1427-1432 application/pdf |
| dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
| publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
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reponame:Repositório Institucional da UNIFESP instname:Universidade Federal de São Paulo (UNIFESP) instacron:UNIFESP |
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Universidade Federal de São Paulo (UNIFESP) |
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UNIFESP |
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UNIFESP |
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Repositório Institucional da UNIFESP |
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Repositório Institucional da UNIFESP |
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Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP) |
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biblioteca.csp@unifesp.br |
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1814268457044148224 |