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Volumn 4, Issue 12, 2002, Pages 2097-2099

Unique Ionic Iodine Atom Transfer Cyclization: A New Route to Iodomethylated Pyrrolidine Derivatives from γ-Iodoolefin and Chloramine-T

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ARTICLE;

EID: 0013282927     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026020i     Document Type: Article
Times cited : (36)

References (27)
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    • For recent reviews, see: (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Pergamon: Oxford, 1996; Vol. 2, pp 119-206. (b) Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. (c) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 1999, 2553-2581. (d) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. (e) Gribble, G. W.; Gilchrist, T. L. Progress in Heterocyclic Chemistry; Pergamon: Oxford, 2001; Vol. 13.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 119-206
    • Sundberg, R.J.1
  • 3
    • 33748495141 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Pergamon: Oxford, 1996; Vol. 2, pp 119-206. (b) Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. (c) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 1999, 2553-2581. (d) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. (e) Gribble, G. W.; Gilchrist, T. L. Progress in Heterocyclic Chemistry; Pergamon: Oxford, 2001; Vol. 13.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3493-3513
    • Nadin, A.1
  • 4
    • 0002393015 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Pergamon: Oxford, 1996; Vol. 2, pp 119-206. (b) Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. (c) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 1999, 2553-2581. (d) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. (e) Gribble, G. W.; Gilchrist, T. L. Progress in Heterocyclic Chemistry; Pergamon: Oxford, 2001; Vol. 13.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 2553-2581
    • Nadin, A.1    Mitchinson, A.2
  • 5
    • 0002936894 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Pergamon: Oxford, 1996; Vol. 2, pp 119-206. (b) Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. (c) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 1999, 2553-2581. (d) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. (e) Gribble, G. W.; Gilchrist, T. L. Progress in Heterocyclic Chemistry; Pergamon: Oxford, 2001; Vol. 13.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 2862-2892
    • Nadin, A.1    Mitchinson, A.2
  • 6
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    • Pergamon: Oxford
    • For recent reviews, see: (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Pergamon: Oxford, 1996; Vol. 2, pp 119-206. (b) Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. (c) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 1999, 2553-2581. (d) Nadin, A.; Mitchinson, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. (e) Gribble, G. W.; Gilchrist, T. L. Progress in Heterocyclic Chemistry; Pergamon: Oxford, 2001; Vol. 13.
    • (2001) Progress in Heterocyclic Chemistry , vol.13
    • Gribble, G.W.1    Gilchrist, T.L.2
  • 8
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    • Pizey, J. S., Ed.; Wiley: New York
    • (b) Bremner, D. H. In Synthetic Reagents; Pizey, J. S., Ed.; Wiley: New York, 1985; Vol. 6, pp 9-59.
    • (1985) Synthetic Reagents , vol.6 , pp. 9-59
    • Bremner, D.H.1
  • 25
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    • In the presence of a catalytic amount of ICl, aziridinations smoothly proceed by the reaction of olefins with CT; see ref 5b
    • In the presence of a catalytic amount of ICl, aziridinations smoothly proceed by the reaction of olefins with CT; see ref 5b.
  • 26
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    • ICl would also generate in situ by the reaction of remaining CT with NaI. See, for example: Kabalka, G. W.; Gooch, E. E. J. Org. Chem. 1981, 46, 2582-2584.
    • (1981) J. Org. Chem. , vol.46 , pp. 2582-2584
    • Kabalka, G.W.1    Gooch, E.E.2
  • 27
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    • Recently, the synthetic route to pyrrolidines via radical [3 + 2] annulation reaction of N-allyl-N-chlorotosylamides with alkenes was reported by Oshima: Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709-2711.
    • (2001) Org. Lett. , vol.3 , pp. 2709-2711
    • Tsuritani, T.1    Shinokubo, H.2    Oshima, K.3


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