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Keywords:

  • Asymmetric catalysis;
  • 1,2-Diphenylethane-1,2-diol;
  • Chiral sulfoxides;
  • Oxidation;
  • Titanium

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)