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Short Communication
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
Article first published online: 21 JAN 2009
DOI: 10.1002/ejoc.200801139
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1099-0690/asset/cover.gif?v=1&s=2cc52719b72cfaff52154639cf010f601d160064 "European Journal of Organic Chemistry")
Additional Information
How to Cite
Jiang, B., Zhao, X.-L., Dong, J.-J. and Wang, W.-J. (2009), 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. European Journal of Organic Chemistry, 2009: 987–991. doi: 10.1002/ejoc.200801139
Publication History
- Issue published online: 17 FEB 2009
- Article first published online: 21 JAN 2009
- Manuscript Received: 17 NOV 2008
Funded by
- Shanghai Municipal Committee of Science and Technology. Grant Number: 05DZ19344
- National Natural Science Foundation of China. Grant Number: 20802087
- Knowledge Innovation Program of the Chinese Academy of Sciences
- Ministry of Science and Technology of the P. R. China
Keywords:
- Asymmetric catalysis;
- 1,2-Diphenylethane-1,2-diol;
- Chiral sulfoxides;
- Oxidation;
- Titanium
Graphical Abstract
Catalytic asymmetric oxidation of sulfides attached to nitrogen-containing heterocyles to chiral sulfoxides with tert-butyl hydroperoxide and a chiral titanium complex, formed in situ from Ti(iPrO)4, chiral 1,2-diphenylethane-1,2-diol 3c and water, was achieved. The chiral sufoxides were obtained in high yield (97 %) with excellent enantiomeric excess of up to 98 % ee.
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)