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Volumn 11, Issue 5, 2009, Pages 1175-1178

Stereoselective double friedel-crafts alkylation of indoles with divinyl ketones

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; KETONE;

EID: 64349087238     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900014a     Document Type: Article
Times cited : (43)

References (78)
  • 21
    • 0036336284 scopus 로고    scopus 로고
    • Rosiak, A.; Christoffers, J. Synlett 2006, 1434. Liljebris, C.; Martinsson, J.; Tedenborg, L.; Williams, M.; Barker, E.; Duffy, J. E. S.; Nygren, A.; James, S. Bioorg. Med. Chem. 2002, 10, 3197.
    • (b) Rosiak, A.; Christoffers, J. Synlett 2006, 1434. Liljebris, C.; Martinsson, J.; Tedenborg, L.; Williams, M.; Barker, E.; Duffy, J. E. S.; Nygren, A.; James, S. Bioorg. Med. Chem. 2002, 10, 3197.
  • 33
    • 64349111762 scopus 로고    scopus 로고
    • Risitano, F.; Grassi, G.; Foti, F.; Romeo, R. Synthesis 2002, 116. Takaya, H.; Murahashi, S. I. Synlett 2001, 991.
    • (f) Risitano, F.; Grassi, G.; Foti, F.; Romeo, R. Synthesis 2002, 116. Takaya, H.; Murahashi, S. I. Synlett 2001, 991.
  • 43
    • 34547859223 scopus 로고    scopus 로고
    • For recent examples of stereoselective indole-enone Friedel-Crafts reactions, see: a
    • For recent examples of stereoselective indole-enone Friedel-Crafts reactions, see: (a) Evans, D. A.; Fandrick, K. R.; Song, H. J.; Scheldt, K. A.; Xu, R. S. J. Am. Chem. Soc. 2007, 129, 10029.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 10029
    • Evans, D.A.1    Fandrick, K.R.2    Song, H.J.3    Scheldt, K.A.4    Xu, R.S.5
  • 60
    • 33748340434 scopus 로고    scopus 로고
    • For a recent review covering examples of intramolecular indole Friedel-Crafts alkylations, see
    • For a recent review covering examples of intramolecular indole Friedel-Crafts alkylations, see: Bandini, M.; Emer, E.; Tommasi, S.; Umani-Ronchi, A. Eur. J. Org. Chem. 2006, 3527.
    • (2006) Eur. J. Org. Chem , pp. 3527
    • Bandini, M.1    Emer, E.2    Tommasi, S.3    Umani-Ronchi, A.4
  • 68
    • 64349122357 scopus 로고    scopus 로고
    • Ketone 2a was prepared through treatment of cinnamic acid Weinreb amide with propenylmagnesium bromide. See Supporting Information for full details.
    • Ketone 2a was prepared through treatment of cinnamic acid Weinreb amide with propenylmagnesium bromide. See Supporting Information for full details.
  • 70
    • 64349117649 scopus 로고    scopus 로고
    • The regiochemistry of 4a was determined by NMR correlation experiments.
    • The regiochemistry of 4a was determined by NMR correlation experiments.
  • 71
    • 64349123721 scopus 로고    scopus 로고
    • The results of this study were first presented by poster at the BOSS XI conference, Gent, Belgium, July 13-18, 2008.
    • The results of this study were first presented by poster at the BOSS XI conference, Gent, Belgium, July 13-18, 2008.
  • 74
    • 64349089548 scopus 로고    scopus 로고
    • No Nazarov cyclopentenone product is observed on treating divinylketone 2 with 5% catalyst 6 in MeCN at room temperature for 60 h.
    • No Nazarov cyclopentenone product is observed on treating divinylketone 2 with 5% catalyst 6 in MeCN at room temperature for 60 h.
  • 78
    • 64349122575 scopus 로고    scopus 로고
    • The possibility of a direct Friedel-Crafts cyclization at indole C-2 exists in the absence of observing the spirocycle II. This mechanistic matter is the focus of ongoing studies.
    • The possibility of a direct Friedel-Crafts cyclization at indole C-2 exists in the absence of observing the spirocycle II. This mechanistic matter is the focus of ongoing studies.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.