Catalytic asymmetric oxidation of 1H-benzimidazolyl pyridinylmethyl sulfides with cumene hydroperoxide catalyzed by a titanium complex with (S,S)-N,N′-dibenzyl tartramide ligand |
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| Authors: | Guoyong Che Jing Xiang Tian Tian Qingfei Huang Linfeng Cun Jian Liao Qiwei Wang Jin Zhu Jingen Deng |
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| Institution: | 1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China;3. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China |
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| Abstract: | A chiral titanium complex, formed in situ from Ti(Oi-Pr)4, (S,S)-N,N′-dibenzyl tartramide and water was found to serve as an efficient catalyst for the asymmetric oxidations of 1H-benzimidazolyl pyridinylmethyl sulfides with cumene hydroperoxide (CHP) in the absence of a base. Several proton pump inhibitors (PPIs), such as esomeprazole, lansoprazole, rabeprazole and pantoprazole were obtained in high yield (up to 92%) and excellent enantiomeric excess (up to 96%). |
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