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Volumn 44, Issue 31, 2003, Pages 5843-5846

Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones

Author keywords

Aluminium; Asymmetric catalysis; Indole; Ketones; Michael reaction

Indexed keywords

ALUMINUM DERIVATIVE; CHLORIDE; INDOLE DERIVATIVE; KETONE;

EID: 0037969443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01400-X     Document Type: Article
Times cited : (96)

References (30)
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    • Chiral aluminium Schiff base complexes have been shown to be effective catalysts in several asymmetric processes: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315-5316; (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960; (c) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888; (d) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5315-5316
    • Sigman, M.S.1    Jacobsen, E.N.2
  • 18
    • 0033615304 scopus 로고    scopus 로고
    • Chiral aluminium Schiff base complexes have been shown to be effective catalysts in several asymmetric processes: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315-5316; (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960; (c) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888; (d) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8959-8960
    • Myers, J.K.1    Jacobsen, E.N.2
  • 19
    • 0035907043 scopus 로고    scopus 로고
    • Chiral aluminium Schiff base complexes have been shown to be effective catalysts in several asymmetric processes: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315-5316; (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960; (c) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888; (d) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1884-1888
    • Evans, D.A.1    Janey, J.M.2    Magomedov, N.3    Tedrow, J.S.4
  • 20
    • 0037448902 scopus 로고    scopus 로고
    • Chiral aluminium Schiff base complexes have been shown to be effective catalysts in several asymmetric processes: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315-5316; (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960; (c) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888; (d) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4442-4443
    • Sammis, G.M.1    Jacobsen, E.N.2
  • 21
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    • The use of cyclic enones such as 2-cyclopenten-1-one and 2-cyclohexen-1-one furnished the desired indolyl derivatives only in traces
    • The use of cyclic enones such as 2-cyclopenten-1-one and 2-cyclohexen-1-one furnished the desired indolyl derivatives only in traces.
  • 22
    • 0037119302 scopus 로고    scopus 로고
    • The role of pyridine as an additive in metallo-salen catalysed asymmetric cyclopropanation of olefins was recently discussed:
    • The role of pyridine as an additive in metallo-salen catalysed asymmetric cyclopropanation of olefins was recently discussed: Miller J.A., Jin W., Nguyen S.T. Angew. Chem., Int. Ed. 41:2002;2953-2956.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2953-2956
    • Miller, J.A.1    Jin, W.2    Nguyen, S.T.3
  • 23
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    • 3N 100 mol%, 18% yield, 66% ee)
    • 3N 100 mol%, 18% yield, 66% ee).
  • 24
    • 85031149836 scopus 로고    scopus 로고
    • note
    • It is also notable that by using an excess of enone 2c (1.5 equiv.) with respect to the indole 3a (1 equiv.), 4ca was obtained with a comparable enantiomeric excess (77%) but with a significantly higher yield (87%).
  • 25
    • 85031154491 scopus 로고    scopus 로고
    • note
    • 2, rt, 300 MHz): 8.34[7.80] (2H, CH=N), 7.58[7.41] (2H, Ar), 7.18[7.03] (2H, Ar).
  • 29
    • 0034674236 scopus 로고    scopus 로고
    • 2' Schiff base aluminium enolates were already utilised as initiators for the methacrylate polymerisation: and references cited therein
    • 2' Schiff base aluminium enolates were already utilised as initiators for the methacrylate polymerisation: Cameron P.A., Gibson V. C., Irvine D.J. Angew. Chem., Int. Ed. 39:2000;2141-2144. and references cited therein.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2141-2144
    • Cameron, P.A.1    Gibson, V.C.2    Irvine, D.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.