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Volumn 66, Issue 7, 2010, Pages 1447-1457

N,N′-Dioxide-scandium(III) complex catalyzed highly enantioselective Friedel-Crafts alkylation of indole to alkylidene malonates

Author keywords

Alkylidene malonates; Friedel crafts alkylation; Indole derivatives; N,N Dioxide scandium(III)

Indexed keywords

ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (2 CHLOROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (2 NAPHTHLY)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (2 THIENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 BROMOPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 CHLOROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 METHOXYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 METHYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 NITROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 PHENOXYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3 TRIFLUOROMETHYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (3,4 DICHLOROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 BROMOPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 CHLOROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 CYANOPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 FLUORO 3 PHENOXYPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 FLUOROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 METHYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 NITROPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (4 TRIFLUOROMETHYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 (CYCLOHEXYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 (3 INDOLYL) 3 PHENYLPROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (4 METHOXYINDOLYL)] 3 PHENYLPROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (5 BROMOINDOLYL)] 3 (3 BROMOPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (5 BROMOINDOLYL)] 3 PHENYLPROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (5 METHOXYINDOLYL)] 3 (4 PHENYLPHENYL)PROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (5 METHOXYINDOLYL)] 3 PHENYLPROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (6 METHOXYINDOLYL)] 3 PHENYLPROPANOATE; ETHYL 2 ETHOXYCARBONYL 3 [3 (7 METHYLINDOLYL)] 3 PHENYLPROPANOATE; INDOLE DERIVATIVE; MALONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 74049088104     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.032     Document Type: Article
Times cited : (29)

References (43)
  • 11
    • 33846613221 scopus 로고    scopus 로고
    • and references therein
    • Adamo M.F.A., and Konda V.R. Org. Lett. 9 (2007) 303-305 and references therein
    • (2007) Org. Lett. , vol.9 , pp. 303-305
    • Adamo, M.F.A.1    Konda, V.R.2
  • 15
    • 74049128453 scopus 로고    scopus 로고
    • For recent reviews on asymmetric Friedel-Crafts reactions, see
    • For recent reviews on asymmetric Friedel-Crafts reactions, see:
  • 29
    • 74049115959 scopus 로고    scopus 로고
    • note
    • Excess indole could be recycled by flash chromatography on silica gel.
  • 30
    • 74049122111 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see:
  • 33
    • 74049104251 scopus 로고    scopus 로고
    • note
    • In the catalytic systems of chiral Cu(II)-oxazoline, ortho-substituted and para-substituted arylidene malonates gave very good results but meta-substituted arylidene malonates were not tolerated (see Ref. 3-5 for details).
  • 38
    • 74049095316 scopus 로고    scopus 로고
    • note
    • Racemic product was obtained in 50% yield.
  • 39
    • 60749133070 scopus 로고    scopus 로고
    • CCDC 704000 contains the supplementary crystallographic data for this paper
    • Liu Y.L., Shang D.J., Zhou X., Liu X.H., and Feng X.M. Chem.- Eur. J. 15 (2009) 2055-2058 CCDC 704000 contains the supplementary crystallographic data for this paper
    • (2009) Chem.- Eur. J. , vol.15 , pp. 2055-2058
    • Liu, Y.L.1    Shang, D.J.2    Zhou, X.3    Liu, X.H.4    Feng, X.M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.