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Volumn 63, Issue 25, 1998, Pages 9455-9461

Deprotection of sulfonyl aziridines

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; BIPHENYL DERIVATIVE; LITHIUM; MAGNESIUM; METHANOL;

EID: 0032509407     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9815296     Document Type: Article
Times cited : (132)

References (70)
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (b) Kump, J. E. G. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 469.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 469
    • Kump, J.E.G.1
  • 32
    • 20644434300 scopus 로고    scopus 로고
    • note
    • Good yields in the desulfonylation reactions were restricted to highly hindered 3-alkyl-2-aryl substituted N-(arenesulfonyl)aziridines.
  • 35
    • 0032482507 scopus 로고    scopus 로고
    • (c) Poor regioselectivities have been recently obtained in the deprotection of N-nosylate protected oxazolidines using Fukuyama's conditions: Wuts, P. G. M.; Northuis, J. M. Tetrahedron Lett. 1998, 39, 3889.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3889
    • Wuts, P.G.M.1    Northuis, J.M.2
  • 42
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    • 5844368669 scopus 로고
    • Pleskov, V. A. Zh. Fiz. Khim. 1937, 9, 12; Acta Physicochim. URSS 1937, 6, 1.
    • (1937) Acta Physicochim. URSS , vol.6 , pp. 1
  • 46
    • 20644438156 scopus 로고    scopus 로고
    • note
    • N-(4-Aminobenzenesulfonyl)-(2S)-benzylaziridine could be isolated as one of the major components of the mixture.
  • 48
    • 20644460067 scopus 로고    scopus 로고
    • note
    • 2.
  • 49
    • 20644456622 scopus 로고
    • For the reduction of arene sulfonamides using Na/naphthalene, see: (a) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 3311. (b) Sugimura, H.; Miura, M.; Yamada, N. Tetrahedron: Asymmetry 1997, 8, 4089. For the reduction of N-substituted tosylamides with lithium and a catalytic amount of naphthalene, see: Alonso, E.; Ramón, D. J., Yus, M. Tetrahedron 1997, 53, 14355.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3311
    • Ji, S.1    Gortler, L.B.2    Waring, A.3    Battisti, A.4    Bank, S.5    Closson, W.D.6    Wriede, P.7
  • 50
    • 0031584584 scopus 로고    scopus 로고
    • For the reduction of arene sulfonamides using Na/naphthalene, see: (a) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 3311. (b) Sugimura, H.; Miura, M.; Yamada, N. Tetrahedron: Asymmetry 1997, 8, 4089. For the reduction of N-substituted tosylamides with lithium and a catalytic amount of naphthalene, see: Alonso, E.; Ramón, D. J., Yus, M. Tetrahedron 1997, 53, 14355.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 4089
    • Sugimura, H.1    Miura, M.2    Yamada, N.3
  • 51
    • 0030841582 scopus 로고    scopus 로고
    • For the reduction of arene sulfonamides using Na/naphthalene, see: (a) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 3311. (b) Sugimura, H.; Miura, M.; Yamada, N. Tetrahedron: Asymmetry 1997, 8, 4089. For the reduction of N-substituted tosylamides with lithium and a catalytic amount of naphthalene, see: Alonso, E.; Ramón, D. J., Yus, M. Tetrahedron 1997, 53, 14355.
    • (1997) Tetrahedron , vol.53 , pp. 14355
    • Alonso, E.1    Ramón, D.J.2    Yus, M.3
  • 53
    • 0027497890 scopus 로고
    • For naphthalene-catalyzed reductive opening of aziridines with lithium, see: (a) Almena, J., Foubelo, F.; Yus, M. Tetrahedron Lett. 1993, 34, 1649. (b) Almena, J., Foubelo, F.; Yus, M. J. Org. Chem. 1994, 59, 3210.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1649
    • Almena, J.1    Foubelo, F.2    Yus, M.3
  • 54
    • 0001453330 scopus 로고
    • For naphthalene-catalyzed reductive opening of aziridines with lithium, see: (a) Almena, J., Foubelo, F.; Yus, M. Tetrahedron Lett. 1993, 34, 1649. (b) Almena, J., Foubelo, F.; Yus, M. J. Org. Chem. 1994, 59, 3210.
    • (1994) J. Org. Chem. , vol.59 , pp. 3210
    • Almena, J.1    Foubelo, F.2    Yus, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.