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Volumn 7, Issue 13, 2001, Pages 2896-2907

Synthesis of functionalized pyrrole and indole derivatives through carbometallation of lithiated double bonds

Author keywords

Carbanions; Carbolithiation; Heterocycles; Indoles; Pyrroles

Indexed keywords

AMINES; COPPER; DIMERIZATION; SYNTHESIS (CHEMICAL);

EID: 0035796535     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010702)7:13<2896::AID-CHEM2896>3.0.CO;2-R     Document Type: Article
Times cited : (43)

References (70)
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    • See for instance, intramolecular aldol, Dieckman, and related enolate cyclizations: a) B. R. Davis, P. J. Garratt in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 806-817;
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    • Davis, B.R.1    Garratt, P.J.2
  • 4
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    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • b) C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 156-176.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 156-176
    • Heathcock, C.H.1
  • 27
    • 0000273487 scopus 로고
    • The preparation of tetrahydrofurans, pyrrolidines, and indolines have been reported by this methodology. a) C. A. Broka, T. Shen, J. Am. Chem. Soc. 1989, 111, 2981;
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2981
    • Broka, C.A.1    Shen, T.2
  • 33
    • 0004628019 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • a) W. Oppolzer in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 31-33;
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 31-33
    • Oppolzer, W.1
  • 39
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press, London
    • c) R. J. Sundberg, Indoles, Academic Press, London, 1996.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 43
    • 0004626284 scopus 로고    scopus 로고
    • note
    • In contrast with our previous report (see ref. [13]), we have observed that the addition of a catalytic ammount of CuCN is not neccesary for the carbometallation step. However, the influence of copper salts as catalyst is being investigated in other organometallic complex derived from 2 and will be reported in due course.
  • 45
    • 0032528237 scopus 로고    scopus 로고
    • The synthesis of some 3,4-bis(trialkylsilylmethyl)-3-pyrrolines have been recently reported by a silylcarbocyclization of 1,6-diynes catalyzed by rhodium complexes: I. Ojima, J. Zhu, E. S. Vidal, D. F. Kass, J. Am. Chem. Soc. 1998, 120, 6690.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6690
    • Ojima, I.1    Zhu, J.2    Vidal, E.S.3    Kass, D.F.4
  • 48
    • 0004569234 scopus 로고    scopus 로고
    • note
    • According to the suggestion of a reviewer, formation of a six-membered ring by a double addition of intermediate 4b to benzil and subsequent retro-Diels-Alder reaction could also lead to the diene 14.
  • 61
    • 0004597994 scopus 로고    scopus 로고
    • note
    • The relative configuration of the stereogenic centers was assigned by taking into account that it was impossible to prepare the corresponding acetonide of 38 h by reaction with 2,2-dimethoxypropane and catalytic amounts of PPTS, together with the absence of NOE between the two adjacent methyl groups in this compound.
  • 69
    • 33847603205 scopus 로고
    • [Chem. Abstr. 1967, 66, 104757f].
    • (1967) Chem. Abstr. , vol.66


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.