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Volumn 126, Issue 42, 2004, Pages 13622-13623

Dirhodium(II) caprolactamate: An exceptional catalyst for allylic oxidation

Author keywords

[No Author keywords available]

Indexed keywords

RHODIUM DERIVATIVE;

EID: 6444238708     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045330o     Document Type: Article
Times cited : (207)

References (43)
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    • For a general review of allylic oxidation see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 7, p 83.
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    • Bulman Page, P.C.1    McCarthy, T.J.2
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    • For asymmetric allylic oxidations see: (a) Andrus, M. B.; Zhou, Z. J. Am. Chum. Soc. 2002, 124, 8806. (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
    • (2002) J. Am. Chum. Soc. , vol.124 , pp. 8806
    • Andrus, M.B.1    Zhou, Z.2
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    • 0037185537 scopus 로고    scopus 로고
    • For asymmetric allylic oxidations see: (a) Andrus, M. B.; Zhou, Z. J. Am. Chum. Soc. 2002, 124, 8806. (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
    • (2002) Tetrahedron , vol.58 , pp. 845
    • Andrus, M.B.1    Lashley, J.C.2
  • 4
    • 0035476406 scopus 로고    scopus 로고
    • For asymmetric allylic oxidations see: (a) Andrus, M. B.; Zhou, Z. J. Am. Chum. Soc. 2002, 124, 8806. (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3567
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    • Recent work: (a) Yu, J.-Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232. (b) Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727. (c) Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 3232
    • Yu, J.-Q.1    Corey, E.J.2
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    • Recent work: (a) Yu, J.-Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232. (b) Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727. (c) Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
    • (2002) Org. Lett. , vol.4 , pp. 2727
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    • Recent work: (a) Yu, J.-Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232. (b) Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727. (c) Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
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    • Selected reviews: (a) Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981. (c) Metal-Catalyzed Selective Oxidations. In Peroxide Chemistry Mechanistic and Preparative Aspects of Oxygen Transfer; Adam, W., Ed.; Wiley: Weinheim, 2000; p 301.
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    • Academic Press: New York
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    • (1981) Metal-Catalyzed Oxidations of Organic Compounds
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    • Metal-Catalyzed Selective Oxidations
    • Selected reviews: (a) Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981. (c) Metal-Catalyzed Selective Oxidations. In Peroxide Chemistry Mechanistic and Preparative Aspects of Oxygen Transfer; Adam, W., Ed.; Wiley: Weinheim, 2000; p 301.
    • (2000) Peroxide Chemistry Mechanistic and Preparative Aspects of Oxygen Transfer , pp. 301
    • Wiley, A.W.1    Weinheim2
  • 23
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    • note
    • Enedione 2 is a nonvolatile solid allowing rapid purification and determination of yield.
  • 24
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    • note
    • Anhydrous tert-butyl hydroperoxide in decane was obtained from Aldrich.
  • 25
    • 6444241955 scopus 로고    scopus 로고
    • note
    • Longer reaction times did not increase yield.
  • 26
    • 6444243339 scopus 로고    scopus 로고
    • note
    • For tert-butyl peroxy ethers as intermediates, see: refs 3a, 3b, and 6c.
  • 28
    • 6444231454 scopus 로고    scopus 로고
    • See Supporting Information for optimization results
    • See Supporting Information for optimization results.
  • 29
    • 6444233226 scopus 로고    scopus 로고
    • note
    • 2) yielded the analytically pure compound.
  • 31
    • 6444221892 scopus 로고    scopus 로고
    • See Supporting Information for UV-visible spectrum
    • See Supporting Information for UV-visible spectrum.
  • 34
    • 6444236687 scopus 로고    scopus 로고
    • note
    • 5+ complex. Efforts are underway to obtain a crystal structure of this complex.
  • 43
    • 6444223436 scopus 로고    scopus 로고
    • note
    • We have isolated 7 (where R = Ph) from the oxidation of 1-phenylcyclohexene. Resubmitting 7 to the reaction resulted in quantitative conversion to the product shown in Table I, entry 3. See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.