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Volumn 63, Issue 25, 1998, Pages 9392-9395

Catalytic asymmetric oxidation of aryl sulfides with a Ti/H2O/(R,R)- diphenylethane-1,2-diol complex: A versatile and highly enantioselective oxidation protocol

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYLETHANE 1,2 DIOL; ETHANE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

EID: 0032509374     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981346j     Document Type: Article
Times cited : (133)

References (44)
  • 1
    • 0001936441 scopus 로고
    • Asymmetric Oxidation of Sulfides
    • Ojima, I., Ed.; VCH: New York
    • Kagan, H. B. Asymmetric Oxidation of Sulfides. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 203-226.
    • (1993) Catalytic Asymmetric Synthesis , pp. 203-226
    • Kagan, H.B.1
  • 2
    • 11944251609 scopus 로고
    • Carreño, 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 & Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 53-94. Posner, G. H. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons, Ltd.: Chichester, England, 1988; Chapter 16, pp 823-849.
    • (1995) Chem. Rev. , vol.95 , pp. 1717
    • Carreño, M.C.1
  • 3
    • 85077702395 scopus 로고
    • Carreño, 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 & Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 53-94. Posner, G. H. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons, Ltd.: Chichester, England, 1988; Chapter 16, pp 823-849.
    • (1981) Synthesis , pp. 185
    • Solladié, G.1
  • 4
    • 0002766558 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons, Ltd.: Chichester, England, Chapter 3
    • Carreño, 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 & Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 53-94. Posner, G. H. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons, Ltd.: Chichester, England, 1988; Chapter 16, pp 823-849.
    • (1988) The Chemistry of Sulfones and Sulfoxides , pp. 53-94
    • Andersen, K.K.1
  • 5
    • 0002335594 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons, Ltd.: Chichester, England, Chapter 16
    • Carreño, 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 & Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 53-94. Posner, G. H. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons, Ltd.: Chichester, England, 1988; Chapter 16, pp 823-849.
    • (1988) The Chemistry of Sulfones and Sulfoxides , pp. 823-849
    • Posner, G.H.1
  • 6
    • 0000108128 scopus 로고
    • Aug 15
    • (a) RP 73163: Pitchen, P. Chem. Ind. 1994, Aug 15, 636.
    • (1994) Chem. Ind. , pp. 636
    • Pitchen, P.1
  • 29
    • 20644452186 scopus 로고    scopus 로고
    • note
    • 4, while a partial decomposition to benzaldehyde results after further addition of TBHP. Moreover, we observed that TBHP alone does not oxidize the sulfoxide while it promotes a slow oxidation of the sulfide.
  • 34
    • 0006420358 scopus 로고
    • The assignment of absolute configuration of sulfoxides via analysis of CD spectra has already been reported: Sagae, T.; Ogawa, S.; Furukawa, N. Bull. Chem. Soc. Jpn. 1991, 64, 3179.
    • (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 3179
    • Sagae, T.1    Ogawa, S.2    Furukawa, N.3
  • 38
    • 0029066475 scopus 로고
    • The importance of π-π interaction in asymmetric synthesis has been recently pointed out: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475. For a recent discussion about the arene-arene interactions see: Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1585. Hunter, C. A. Chem. Soc. Rev. 1994, 101. Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 1995.
    • (1995) Synthesis , pp. 475
    • Jones, G.B.1    Chapman, B.J.2
  • 39
    • 0000056388 scopus 로고
    • The importance of π-π interaction in asymmetric synthesis has been recently pointed out: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475. For a recent discussion about the arene-arene interactions see: Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1585. Hunter, C. A. Chem. Soc. Rev. 1994, 101. Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 1995.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1585
    • Hunter, C.A.1
  • 40
    • 0001894947 scopus 로고
    • The importance of π-π interaction in asymmetric synthesis has been recently pointed out: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475. For a recent discussion about the arene-arene interactions see: Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1585. Hunter, C. A. Chem. Soc. Rev. 1994, 101. Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 1995.
    • (1994) Chem. Soc. Rev. , pp. 101
    • Hunter, C.A.1
  • 41
    • 0001579080 scopus 로고
    • The importance of π-π interaction in asymmetric synthesis has been recently pointed out: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475. For a recent discussion about the arene-arene interactions see: Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1585. Hunter, C. A. Chem. Soc. Rev. 1994, 101. Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 1995.
    • (1995) Pure Appl. Chem. , vol.67 , pp. 1995
    • Cozzi, F.1    Siegel, J.S.2
  • 42
    • 20644432369 scopus 로고    scopus 로고
    • note
    • It is interesting to point out that also in Ti-trialkanolamine catalyzed oxidations, (see ref 6d) the highest enantioselectivity (ee 84%) is achieved when phenyl benzyl sulfide is oxidized with the (R,R,R)-tris(2-hydroxy-2-phenylethyl)amine complex, i.e., with a ligand bearing phenyl groups.


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