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Synthesis 2004(2): 217-220  
DOI: 10.1055/s-2003-44365
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Optically Active α,β-Unsaturated Triazolyl Alcohols via Chiral Auxiliary-Modified NaBH4 Reduction of the Corresponding Ketones

Zhou Zhenghong, Tang Yilong, Wang Lixin, Zhao Guofeng, Zhou Qilin, Tang Chuchi*
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Fax: +86(22)23503438; e-Mail: c.c.tang@eyou.com;
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Publication History

Received 12 September 2003
Publication Date:
09 December 2003 (online)

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Abstract

α-Disubstituted pyrrolidine-2-methanols were synthesized starting from l-proline and their application as chiral auxiliary in the asymmetric NaBH4 reduction of α,β-unsaturated triazolyl ketones was investigated. The corresponding α,β-unsaturated triazolyl alcohol derivatives (Uniconazole and Diniconazole) were obtained in good chemical yields with high ee values (up to 93%).

Key words

triazoles - l-proline - asymmetric reduction

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