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

Journal of the Brazilian Chemical Society

Rocha, Lenilson C.¹  Porto, André L. M.¹  Raminelli, Cristiano¹  Rosset, Isac G.¹  Melgar, Gliseida Z.¹  Universidade Federal de São Paulo, Diadema, Brazil¹  Jeller, Alex H.¹  Universidade de São Paulo, São Carlos, Brazil¹  Universidade Estadual de Mato Grosso do Sul, Dourados, Brazil¹ 

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

DOI  :  10.5935/0103-5053.20130181

学科分类：化学（综合）

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】

Unknown