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

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

Author Rocha, Lenilson Coutinho Google Scholar
Rosset, Isac George Google Scholar
Melgar, Gliseida Zelayaran Google Scholar
Raminelli, Cristiano Autor UNIFESP Google Scholar
Porto, André Luiz Meleiro Google Scholar
Jeller, Alex Haroldo Google Scholar
Institution Universidade de São Paulo (USP)
Universidade Federal de São Paulo (UNIFESP)
Universidade Estadual de Mato Grosso do Sul Coordenação de Química
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.

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.
Keywords CALB
lipase
biocatalysis
click chemistry
[3 + 2]
cycloaddition
Language English
Sponsor Fundação 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)
Date 2013-09-01
Published in Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 24, n. 9, p. 1427-1432, 2013.
ISSN 0103-5053 (Sherpa/Romeo, impact factor)
1678-4790 (Sherpa/Romeo, impact factor)
Publisher Sociedade Brasileira de Química
Extent 1427-1432
Origin http://dx.doi.org/10.5935/0103-5053.20130181
Access rights Open access Open Access
Type Article
Web of Science ID WOS:000324933300006
SciELO ID S0103-50532013000900006 (statistics in SciELO)
URI http://repositorio.unifesp.br/handle/11600/7957

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