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Volumn 71, Issue 17, 2006, Pages 6655-6658

Cobalt-catalyzed aziridination with diphenylphosphoryl azide (DPPA): Direct synthesis of N-phosphorus-substituted aziridines from alkenes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COBALT; COMPLEXATION; OLEFINS; SYNTHESIS (CHEMICAL); TRACE ANALYSIS;

EID: 33747469456     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0609226     Document Type: Article
Times cited : (100)

References (65)
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    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (b) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2. p 607.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 607
    • Jacobsen, E.N.1
  • 24
    • 0345802957 scopus 로고    scopus 로고
    • For a recent Ag-based aziridination system, see: Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 16202
    • Cui, Y.1    He, C.2
  • 37
    • 0001627927 scopus 로고
    • For examples of biomedical applications of N-phosphorus-substituted aziridines, see: (a) Perlman, M. E.; Bardos, T. J. J. Org. Chem. 1988, 53, 1761.
    • (1988) J. Org. Chem. , vol.53 , pp. 1761
    • Perlman, M.E.1    Bardos, T.J.2
  • 39
    • 33747511913 scopus 로고    scopus 로고
    • note
    • A N-phosphorylated aziridine was recently synthesized in 33% yield via Rh-catalyzed aziridination. See ref 5c.
  • 40
    • 0003641908 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds. Academic Press: San Diego, CA
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds. The Porphyrin Handbook; Academic Press: San Diego, CA, 2000-2003; Vols. 1-20.
    • (2000) The Porphyrin Handbook , vol.1-20
  • 43
    • 0037414525 scopus 로고    scopus 로고
    • For our recent efforts on metalloporphyrin-catalyzed analogous carbene transfer reactions, see: (a) Chen, Y.; Huang, L.; Ranade, M. A.; Zhang, X. P. J. Org. Chem. 2003, 68, 3714.
    • (2003) J. Org. Chem. , vol.68 , pp. 3714
    • Chen, Y.1    Huang, L.2    Ranade, M.A.3    Zhang, X.P.4
  • 52
    • 33845552528 scopus 로고
    • Metalloporphyrins represent the first transition metal complexes for catalyzing aziridination. See: (a) Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2073
    • Groves, J.T.1    Takahashi, T.2
  • 59
    • 0015520853 scopus 로고
    • The commercially available, low cost diphenylphosphoryl azide is a stable and distillable liquid that has been widely used in various organic syntheses. For selected examples, see: (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6203
    • Shioiri, T.1    Ninomiya, K.2    Yamada, S.3
  • 63
    • 33747499646 scopus 로고    scopus 로고
    • note
    • 2 was shown to catalyze aziridination of styrene with bromamine-T to form the desired aziridine in 56% yield. See ref 7a.
  • 65
    • 33747483885 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, the only other example of aziridination of pentafluorostyrene was previously reported by us with a cobalt porphyrin/bromamine-T catalytic system. See ref 16b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.