Catalytic asymmetric oxidation of 1H-benzimidazolyl pyridinylmethyl sulfides with cumene hydroperoxide catalyzed by a titanium complex with (S,S)-N,N′-dibenzyl tartramide ligand

Guoyong Che,Jing Xiang,Tian Tian,Qingfei Huang,Linfeng Cun,Jian Liao,Qiwei Wang,Jin Zhu,Jingen Deng

doi:10.1016/j.tetasy.2012.03.017

Catalytic asymmetric oxidation of 1H-benzimidazolyl pyridinylmethyl sulfides with cumene hydroperoxide catalyzed by a titanium complex with (S,S)-N,N′-dibenzyl tartramide ligand

Guoyong Che, Jing Xiang + Show 7 more

https://doi.org/10.1016/j.tetasy.2012.03.017

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Journal: Tetrahedron: Asymmetry	Publication Date: Apr 1, 2012
Citations: 15

Affiliation: Chengdu Organic Chemicals (China), Chinese Academy of Sciences, Sichuan University

#Chiral Titanium Complex #Proton Pump Inhibitors + Show 8 more

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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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