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

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 enantiomerical...

Full description

Bibliographic Details
Published in:Journal of the Brazilian Chemical Society
Main Authors: Rocha, Lenilson Coutinho, Rosset, Isac George, Melgar, Gliseida Zelayaran, Raminelli, Cristiano UNIFESP, Porto, André Luiz Meleiro, Jeller, Alex Haroldo
Other Authors: Universidade de São Paulo (USP), Universidade Federal de São Paulo (UNIFESP), Universidade Estadual de Mato Grosso do Sul Coordenação de Química
Format: Article in Journal/Newspaper
Language:English
Published: Sociedade Brasileira de Química 2013
Subjects:
CALB
lipase
biocatalysis
click chemistry
[3 + 2]
cycloaddition
Antarc*
Antarctica
Online Access:http://repositorio.unifesp.br/handle/11600/7957
https://doi.org/10.5935/0103-5053.20130181
Description
Summary: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. 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) Universidade de São Paulo Instituto de Química de São Carlos Universidade Federal de São Paulo (UNIFESP) Departamento de Ciências Exatas e da Terra Universidade Estadual de Mato Grosso do Sul Coordenação de Química UNIFESP, Depto. de Ciências Exatas e da Terra SciELO

Similar Items