Catalytic asymmetric oxidation of aryl methyl sulfides mediated by a (S,S)-1,2-diphenylethan-1,2-diol/titanium/ water complex

Tetrahedron Asymmetry

Volumn 8, Issue 3, 1997, Pages 349-352

  Superchi, Stefano ^a   Rosini, Carlo ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL SULFIDE; HYDROPEROXIDE; SULFOXIDE;

ARTICLE; CATALYSIS; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME;

EID: 0031054768     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00534-4     Document Type: Article

References (20)

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2. Carrẽno, M. C. Chem. Rev. 1995, 95, 1717. Solladié, G. Synthesis 1981, 185. Andersen, K. K. In The Chemistry of Sulfones and Sulfoxides, Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons, Ltd.: Chichester, England, 1988; Chapter 16, pp 823-849.
3. Carrẽno, M. C. Chem. Rev. 1995, 95, 1717. Solladié, G. Synthesis 1981, 185. Andersen, K. K. In The Chemistry of Sulfones and Sulfoxides, Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons, Ltd.: Chichester, England, 1988; Chapter 16, pp 823-849.
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17. GLC-MS revealed the presence of 1,2-diphenylethan-1,2-dione, 1,2-diphenylethanone, 1,1-diphenyl-ethanone and benzaldehyde.
18. 2O as eluent) isolating the phenyl methyl sulfoxide in 60% yield.
19. (R,R)-diethyl tartrate despite an inversion due to the CIP rules, has the same stereostructure of (S,S)-1.
20. The CSP Daicel Chiralcel OB has been used also by other authors (ref. 4a) to separate chiral sulfoxides.