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Volumn , Issue 13, 2005, Pages 2198-2204

Synthesis of α-(3-indolyl)glycine derivatives via spontaneous Friedel-Crafts reaction between indoles and glyoxylate imines

Author keywords

Friedel Crafts reaction; Glyoxylate imine; Indole derivative; Indolyl glycine; Spontaneous reaction

Indexed keywords

CATALYSTS; DERIVATIVES; FRIEDEL-CRAFTS REACTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 23944521388     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869978     Document Type: Article
Times cited : (50)

References (43)
  • 1
    • 33645474490 scopus 로고
    • US Patent, 3316260, 1967
    • (a) Shen, T.-Y. US Patent, 3316260, 1967; Chem. Abstr. 1968, 86, P49447u.
    • (1968) Chem. Abstr. , vol.86
    • Shen, T.-Y.1
  • 19
    • 14844321880 scopus 로고    scopus 로고
    • (b) A most recent example using 1.2 equivalents of a strained chiral silane reagent as Lewis acid: Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 2858.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 2858
    • Shirakawa, S.1    Berger, R.2    Leighton, J.L.3
  • 40
    • 0037017031 scopus 로고    scopus 로고
    • Commercially available reagent: Fluke #50705, Lancaster #19207 and TCI#G0264. Control experiments gave similar results using ethyl glyoxylate (or its hydrate) prepared according to the literature: (a) Bailey, P. D.; Smith, P. D.; Pederson, F.; Clegg, W.; Rosair, G. M.; Teat, S. J. Tetrahedron Lett. 2002, 43, 1067.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1067
    • Bailey, P.D.1    Smith, P.D.2    Pederson, F.3    Clegg, W.4    Rosair, G.M.5    Teat, S.J.6
  • 42
    • 33645490271 scopus 로고    scopus 로고
    • note
    • 2H, MsOH, etc.), the yields were not improved and the diastereoselectivities were deteriorated in the following study.
  • 43
    • 33645484206 scopus 로고    scopus 로고
    • note
    • 2 (5 atm), EtOH, r.t., 24 h, 41% yield of (+)-ethyl (3-indolyl)glycinate (21).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.