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Volumn 8, Issue 11, 2006, Pages 2349-2352

Iron-catalyzed imination of sulfoxides and sulfides

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EID: 33745697784     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060640s     Document Type: Article
Times cited : (125)

References (73)
  • 13
  • 20
    • 0001017993 scopus 로고
    • Reviews concerning sulfoximines and sulfilimines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.
    • (1973) Acc. Chem. Res. , vol.6 , pp. 341
    • Johnson, C.R.1
  • 28
    • 33745688073 scopus 로고    scopus 로고
    • Budavari, S., Ed.; Merck & Co., Inc.: Rahway, NJ
    • 3, see: (d) Merck Index. 12th ed.; Budavari, S., Ed.; Merck & Co., Inc.: Rahway, NJ, 1996; p 451.
    • (1996) Merck Index. 12th Ed. , pp. 451
  • 45
    • 29344457003 scopus 로고    scopus 로고
    • See also in: (g) Katsuki, T. Chem. Lett. 2005, 34, 1304.
    • (2005) Chem. Lett. , vol.34 , pp. 1304
    • Katsuki, T.1
  • 56
    • 26844488178 scopus 로고    scopus 로고
    • For a recent contribution on metal-free iminations allowing access to NH derivatives, see: Cho, G. Y.; Bolm, C. Tetrahedron Lett. 2005, 46, 8007.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 8007
    • Cho, G.Y.1    Bolm, C.2
  • 57
    • 33745702264 scopus 로고    scopus 로고
    • note
    • 2 hampered the conversion, providing sulfoximine 2 in a moderate yield (57%).
  • 58
    • 33745730295 scopus 로고    scopus 로고
    • note
    • 2 here used. Attempts to determine the precise nature of the Fe species remained inconclusive.
  • 59
    • 33745716322 scopus 로고    scopus 로고
    • note
    • 3], is also a good catalyst under these reaction conditions, furnishing 2 in 97% yield after 45 min.
  • 60
    • 0003463148 scopus 로고    scopus 로고
    • John Wiley & Sons: New York
    • For example, nosyl- and benzothiazolesulfonylamides can be easily cleaved using thiolates, SES-amide react upon treatment with fluorides to give amines, and deprotection of the pyridinyl derivative could be achieved by reaction with Mg. For general methods for the deprotection of sulfonylamides, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; p 603.
    • (1999) Protective Groups in Organic Synthesis, 3rd Ed. , pp. 603
    • Greene, T.W.1    Wuts, P.G.M.2
  • 65
    • 33745730293 scopus 로고    scopus 로고
    • note
    • R(S): 48.9 min.
  • 66
    • 33745716321 scopus 로고    scopus 로고
    • note
    • 1H NMR on the crude mixture.
  • 67
    • 33745730292 scopus 로고    scopus 로고
    • note
    • 3 and thiophenol, and at elevated temperature decomposition occurred.
  • 72
    • 33745730294 scopus 로고    scopus 로고
    • note
    • In Scheme 2, we suggest the involvement of Fe(III) and Fe(V) species. However, it is possible that the iron intermediates have other oxidation states.
  • 73
    • 33745688068 scopus 로고    scopus 로고
    • note
    • 4 (Aldrich prices per gram in 2005/2006).


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