4.5 Article

Enantioselective sulfide oxidation catalyzed by 2,10-camphanediol derived titanium complex and its mechanism

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 26, Issue 8, Pages 1435-1439

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.200890261

Keywords

enantioselective catalysis; sulfide oxidation; 2,10-camphanediol; titanium complex; mechanism; ESI-MS

Funding

  1. National Natural Science Foundation of China [20672088]
  2. Chengdu University of Technology [HY0011]

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Cumyl hydroperoxide (CHP) and tert-butyl hydroperoxide (TBHP) produced (R)- and (S)-sulfoxide in 2,10-camphanediol-titanium catalyzed sulfoxidation, respectively. During kinetic resolution, the sulfoxide configuration was reversed with CHP, but kept with TBHP. Based oil these results and the ESI-MS data, the mechanism of sulfoxidation was proposed to be intramolecular nucleophilic oxygen transfer a coordinated sulfide.

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