Catalytic Asymmetric Oxidation of Heteroaromatic Sulfides with tert-Butyl Hydroperoxide Catalyzed by a Titanium Complex with a New Chiral 1,2-Diphenylethane-1,2-diol Ligand

Authors

  • Biao Jiang,

    1. CAS Key Laboratory of Synthetic Chemistry of Natural Substance, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: +86-21-64166128
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  • Xiao-Long Zhao,

    1. CAS Key Laboratory of Synthetic Chemistry of Natural Substance, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: +86-21-64166128
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  • Jia-Jia Dong,

    1. CAS Key Laboratory of Synthetic Chemistry of Natural Substance, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: +86-21-64166128
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  • Wan-Jun Wang

    1. CAS Key Laboratory of Synthetic Chemistry of Natural Substance, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 354 Fenglin Road, Shanghai 200032, P. R. China, Fax: +86-21-64166128
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Abstract

Heteroaromatic sulfoxides, especially 1H-benzimidazolylpyridinylmethyl sulfoxides, usually used as the blockbuster gastric proton pump inhibitors (PPIs), have been prepared highly enantioselectivily by catalytic asymmetric oxidation of sulfides attached to nitrogen-containing heterocyles with tert-butyl hydroperoxide in the presence of a chiral titanium complex, formed in situ from Ti(iPrO)4, chiral 1,2-diphenylethane-1,2-diol 3c and water. The chiral sufoxides were obtained in high yield (97 %) with excellent enantiomeric excess (up to 98 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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