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Synthesis 2008(16): 2513-2518  
DOI: 10.1055/s-2008-1067185
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Optically Active 2,5-Dialkylcyclohexane-1,4-diols and Their Application in the Asymmetric Oxidation of Sulfides

Jiangtao Sun*a,b, Minghua Yanga, Zhenya Daia, Chengjian Zhu*a,c, Hongwen Hua
a Department of Chemistry, Nanjing University, Nanjing 210093, P. R. of China
e-Mail: cjzhu@nju.edu.cn;
b Department of Chemistry, Sundia MediTech (Shanghai) Co, Ltd., Shanghai 201203, P. R. of China
e-Mail: jtsun@sundia.com;
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(21)51903505;
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Received 4 April 2008
Publikationsdatum:
24. Juli 2008 (online)

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Abstract

A simple and efficient approach to obtain optically pure 1,4-diols was established. The asymmetric oxidation of sulfides to sulfoxides with cumyl hydroperoxide in moderate yields and moderate to high enantioselectivities (up to 84%) catalyzed by chiral Ti/1,4-diols complexes has been achieved. A 76% ee value was obtained in the asymmetric synthesis of esomeprazole.

Key words

asymmetric oxidation - sulfide - sulfoxide - titanium - resolution