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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
Author(s) -
Jiang Biao,
Zhao XiaoLong,
Dong JiaJia,
Wang WanJun
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801139
Subject(s) - chemistry , catalysis , titanium , yield (engineering) , tert butyl hydroperoxide , chiral ligand , ligand (biochemistry) , enantiomeric excess , medicinal chemistry , enantiomer , sulfoxide , enantioselective synthesis , diol , organic chemistry , biochemistry , materials science , receptor , metallurgy
Heteroaromatic sulfoxides, especially 1 H ‐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( i PrO) 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)