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Volumn , Issue 19, 2006, Pages 4500-4509

Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation

Author keywords

Asymmetric catalysis; Enantioselectivity; Kinetic resolution; Oxidation; Sulfoxides

Indexed keywords


EID: 33749452984     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600320     Document Type: Article
Times cited : (43)

References (47)
  • 35
    • 33749439094 scopus 로고    scopus 로고
    • note
    • [8f]
  • 36
    • 33749449522 scopus 로고    scopus 로고
    • note
    • In some cases the extent of oxidation is beyond what would be expected on the basis of the amount of oxidant employed. This is possibly due to variation in the concentration of the hydrogen peroxide.
  • 44
    • 33749449695 scopus 로고    scopus 로고
    • note
    • The thiolate anion was generated by treatment of the thiol with an excess of sodium ethoxide. The thiolate anion was then treated with an equimolar amount of benzyl halide and stirred for 16 h at room temperature. Analytical data: for 3a, 3d and 3f: H. Stephenson, N. Clark, J. Marshall, D. Greenwood, D. Higgons, R. Brookes, GB 790197, 1958; for 3b, 3c and 3f: H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 2006, 47, 93-97; for 3e: T. Sagae, S. Owaga, N. Furukawa, Bull. Chem. Soc. Jpn. 1991, 64, 3179-3181; for 3i: C. R. Strauss, H. G. Guay, H. J. Harwood, J. Org. Chem. 1964, 29, 1945-1948.
  • 45
    • 33749430720 scopus 로고    scopus 로고
    • note
    • The sulfoxide was dissolved in acetone at 0°C and 0.5 equivalents of Oxone® dissolved in water was added dropwise. The reaction was monitored by TLC. Analytical data for racemic sulfoxides: 2a and 2f: H. Stephenson, N. Clark, J. Marshall, D. Greenwood, D. Higgons, R. Brookes, GB 790197, 1958; for 2b, 2e and 2h: A. R. Katritzky, B. Z. Yang, Y. F. Qian, Synlett 1996, 701-702; for 2d: B. J. Auret, D. R. Boyd, H. B. Henlest, Chem. Commun. (London) 1966, 3, 66-67; for 2e: T. Sagae, S. Owaga, N. Furukawa, Bull. Chem. Soc. Jpn. 1991, 64, 3179-3181; for 2i: G. A. Russell, J. M. Pecoraro, J. Org. Chem. 1979, 44, 3990-3991; for 2j: K. Nishihata, M. Nishio, Tetrahedron Lett. 1972, 13, 4839-4840.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.