Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles

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dc.contributor.author Rocha, Lenilson Coutinho
dc.contributor.author Rosset, Isac George
dc.contributor.author Melgar, Gliseida Zelayaran
dc.contributor.author Raminelli, Cristiano [UNIFESP]
dc.contributor.author Porto, André Luiz Meleiro
dc.contributor.author Jeller, Alex Haroldo
dc.date.accessioned 2015-06-14T13:45:37Z
dc.date.available 2015-06-14T13:45:37Z
dc.date.issued 2013-09-01
dc.identifier http://dx.doi.org/10.5935/0103-5053.20130181
dc.identifier.citation Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 24, n. 9, p. 1427-1432, 2013.
dc.identifier.issn 0103-5053
dc.identifier.issn 1678-4790
dc.identifier.uri http://repositorio.unifesp.br/handle/11600/7957
dc.description.abstract 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. en
dc.description.abstract 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. pt
dc.description.sponsorship Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorship Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorship Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.format.extent 1427-1432
dc.language.iso eng
dc.publisher Sociedade Brasileira de Química
dc.relation.ispartof Journal of the Brazilian Chemical Society
dc.rights Acesso aberto
dc.subject CALB en
dc.subject lipase en
dc.subject biocatalysis en
dc.subject click chemistry en
dc.subject [3 + 2] en
dc.subject cycloaddition en
dc.title Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles en
dc.type Artigo
dc.contributor.institution Universidade de São Paulo (USP)
dc.contributor.institution Universidade Federal de São Paulo (UNIFESP)
dc.contributor.institution Universidade Estadual de Mato Grosso do Sul Coordenação de Química
dc.description.affiliation Universidade de São Paulo Instituto de Química de São Carlos
dc.description.affiliation Universidade Federal de São Paulo (UNIFESP) Departamento de Ciências Exatas e da Terra
dc.description.affiliation Universidade Estadual de Mato Grosso do Sul Coordenação de Química
dc.description.affiliationUnifesp UNIFESP, Depto. de Ciências Exatas e da Terra
dc.identifier.file S0103-50532013000900006.pdf
dc.identifier.scielo S0103-50532013000900006
dc.identifier.doi 10.5935/0103-5053.20130181
dc.description.source SciELO
dc.identifier.wos WOS:000324933300006



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