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Synlett 2005(16): 2433-2436  
DOI: 10.1055/s-2005-872691
LETTER
© Georg Thieme Verlag Stuttgart · New York

d-Aminoacylase-Catalyzed Markovnikov Addition of Azoles to Vinyl Esters in Organic Solvents

Wei-Bo Wu, Jian-Ming Xu, Qi Wu, De-Shui Lv, Xian-Fu Lin*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87952618; e-Mail: llc123@css.zju.edu.cn;
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Publication History

Received 25 July 2005
Publication Date:
21 September 2005 (online)

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Abstract

A novel strategy to effect Markovnikov addition between azoles and vinyl esters was developed, in which a ‘promiscuous’ enzyme, d-aminoacylase from Escherichia coli, was utilized as the catalyst. The enzymatic Markovnikov addition is dependent on the organic solvent chosen. By this strategy, a series of pharmaceutically active azole derivatives were synthesized in moderate to ­excellent yields.

Key words

enzymes - addition reactions - vinyl esters - d-amino­acylase - catalysis