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Volumn 132, Issue 24, 2010, Pages 8282-8284

Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines

Author keywords

[No Author keywords available]

Indexed keywords

CARBON NUCLEOPHILES; COUPLING REACTION; HETEROCYCLES;

EID: 77953634869     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103428y     Document Type: Article
Times cited : (69)

References (42)
  • 9
    • 34547166889 scopus 로고    scopus 로고
    • For reviews that discuss quaternary-substituted indolines, see
    • For reviews that discuss quaternary-substituted indolines, see: Steven, A. and Overman, L. E. Angew. Chem., Int. Ed. 2007, 46, 5488-5508
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 5488-5508
    • Steven, A.1    Overman, L.E.2
  • 14
    • 61949486967 scopus 로고    scopus 로고
    • For recent examples, see ref 5 and
    • For recent examples, see ref 5 and: Eastman, K. and Baran, P. S. Tetrahedron 2009, 65, 3149-3154
    • (2009) Tetrahedron , vol.65 , pp. 3149-3154
    • Eastman, K.1    Baran, P.S.2
  • 33
    • 0019214697 scopus 로고
    • A bicyclo[2.1.0]pyrrolidine analogue has been isolated from the fermentation of Streptomyces azomyceticus. See
    • A bicyclo[2.1.0]pyrrolidine analogue has been isolated from the fermentation of Streptomyces azomyceticus. See: Kodama, Y. and Ito, T. Agric. Biol. Chem. 1980, 44, 73-76
    • (1980) Agric. Biol. Chem. , vol.44 , pp. 73-76
    • Kodama, Y.1    Ito, T.2
  • 34
    • 0037884930 scopus 로고    scopus 로고
    • For reviews of the synthesis and reactivity of donor-acceptor cyclopropanes, see
    • For reviews of the synthesis and reactivity of donor-acceptor cyclopropanes, see: Reissig, H.-U. and Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
    • (2003) Chem. Rev. , vol.103 , pp. 1151-1196
    • Reissig, H.-U.1    Zimmer, R.2
  • 37
    • 77953643729 scopus 로고    scopus 로고
    • Density functional theory (DFT)-calculated bond lengths for 5 matched the observed reactivity pattern (see Table 2 for the numbering scheme): C(2)-C(4) = 1.57 Å, C(3)-C(4) = 1.48 Å, and C(2)-C(3) = 1.51 Å. See the Supporting Information for details
    • Density functional theory (DFT)-calculated bond lengths for 5 matched the observed reactivity pattern (see Table 2 for the numbering scheme): C(2)-C(4) = 1.57 Å, C(3)-C(4) = 1.48 Å, and C(2)-C(3) = 1.51 Å. See the Supporting Information for details.
  • 38
    • 0030882524 scopus 로고    scopus 로고
    • N2 addition to the cyclopropane leads to product formation. A more detailed mechanistic investigation is a subject for future work. For a discussion of related cyclopropane ring-opening reactions in the CC-1065 and duocarmycin families, see
    • N2 addition to the cyclopropane leads to product formation. A more detailed mechanistic investigation is a subject for future work. For a discussion of related cyclopropane ring-opening reactions in the CC-1065 and duocarmycin families, see: Boger, D. L. and Turnbull, P. J. Org. Chem. 1997, 62, 5849-5863
    • (1997) J. Org. Chem. , vol.62 , pp. 5849-5863
    • Boger, D.L.1    Turnbull, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.