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

Journal of the Brazilian Chemical Society

Lenilson C. Rocha²  Isac G. Rosset²  Gliseida Z. Melgar²  Cristiano Raminelli¹  André L. M. Porto²  Alex H. Jeller² 

[1] ,Universidade de São Paulo Instituto de Química de São Carlos São Carlos SP ,Brazil

关键词: CALB;    lipase;    biocatalysis;    click chemistry;    [3 + 2];    cycloaddition;   

DOI  :  10.5935/0103-5053.20130181

来源: SciELO

【 摘 要 】

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.

【 授权许可】

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