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Volumn 68, Issue 11, 2003, Pages 4594-4597

The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3·7H2O-NaI combination supported on silica gel

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKYLATION; CATALYSIS; CATALYST SUPPORTS; CERIUM COMPOUNDS; DERIVATIVES; REACTION KINETICS; SILICA GEL; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

EID: 0037764697     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034303y     Document Type: Article
Times cited : (192)

References (55)
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    • note
    • Dedicated to Prof. Domenico Spinelli the occasion of his 70th birthday.
  • 2
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    • (b) Trost, B. M. Science 1991, 254, 1471.
    • (1991) Science , vol.254 , pp. 1471
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  • 44
    • 57249112162 scopus 로고    scopus 로고
    • For some applications of catalysts adsorbed on silica gel, see: (a) Benerjee, A. K.; Laya Mimó, M. S.; Vera Vegas, W. J. Russ. Chem. Rev. 2001, 70, 971. (b) Bianchini, C.; Burnaby, D. G.; Evans, J.; Frediani, P.; Meli, A.; Oberhause, W.; Psaro, R.; Vizza, F. J. Am. Chem. Soc. 1999, 121, 5961. (c) Anson, M. S.; Mirza, A. R.; Touks, L.; Williams, J. M. J. Tetrahedron Lett. 1999, 40, 7147. (d) Davis, M. E. Chemtec 1992, 498. (e) Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hauson, B. E. Nature 1989, 339, 454.
    • (2001) Russ. Chem. Rev. , vol.70 , pp. 971
    • Benerjee, A.K.1    Laya Mimó, M.S.2    Vera Vegas, W.J.3
  • 45
    • 0033618082 scopus 로고    scopus 로고
    • For some applications of catalysts adsorbed on silica gel, see: (a) Benerjee, A. K.; Laya Mimó, M. S.; Vera Vegas, W. J. Russ. Chem. Rev. 2001, 70, 971. (b) Bianchini, C.; Burnaby, D. G.; Evans, J.; Frediani, P.; Meli, A.; Oberhause, W.; Psaro, R.; Vizza, F. J. Am. Chem. Soc. 1999, 121, 5961. (c) Anson, M. S.; Mirza, A. R.; Touks, L.; Williams, J. M. J. Tetrahedron Lett. 1999, 40, 7147. (d) Davis, M. E. Chemtec 1992, 498. (e) Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hauson, B. E. Nature 1989, 339, 454.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5961
    • Bianchini, C.1    Burnaby, D.G.2    Evans, J.3    Frediani, P.4    Meli, A.5    Oberhause, W.6    Psaro, R.7    Vizza, F.8
  • 46
    • 0033600767 scopus 로고    scopus 로고
    • For some applications of catalysts adsorbed on silica gel, see: (a) Benerjee, A. K.; Laya Mimó, M. S.; Vera Vegas, W. J. Russ. Chem. Rev. 2001, 70, 971. (b) Bianchini, C.; Burnaby, D. G.; Evans, J.; Frediani, P.; Meli, A.; Oberhause, W.; Psaro, R.; Vizza, F. J. Am. Chem. Soc. 1999, 121, 5961. (c) Anson, M. S.; Mirza, A. R.; Touks, L.; Williams, J. M. J. Tetrahedron Lett. 1999, 40, 7147. (d) Davis, M. E. Chemtec 1992, 498. (e) Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hauson, B. E. Nature 1989, 339, 454.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7147
    • Anson, M.S.1    Mirza, A.R.2    Touks, L.3    Williams, J.M.J.4
  • 47
    • 0038023854 scopus 로고
    • For some applications of catalysts adsorbed on silica gel, see: (a) Benerjee, A. K.; Laya Mimó, M. S.; Vera Vegas, W. J. Russ. Chem. Rev. 2001, 70, 971. (b) Bianchini, C.; Burnaby, D. G.; Evans, J.; Frediani, P.; Meli, A.; Oberhause, W.; Psaro, R.; Vizza, F. J. Am. Chem. Soc. 1999, 121, 5961. (c) Anson, M. S.; Mirza, A. R.; Touks, L.; Williams, J. M. J. Tetrahedron Lett. 1999, 40, 7147. (d) Davis, M. E. Chemtec 1992, 498. (e) Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hauson, B. E. Nature 1989, 339, 454.
    • (1992) Chemtec , pp. 498
    • Davis, M.E.1
  • 48
    • 33748465619 scopus 로고
    • For some applications of catalysts adsorbed on silica gel, see: (a) Benerjee, A. K.; Laya Mimó, M. S.; Vera Vegas, W. J. Russ. Chem. Rev. 2001, 70, 971. (b) Bianchini, C.; Burnaby, D. G.; Evans, J.; Frediani, P.; Meli, A.; Oberhause, W.; Psaro, R.; Vizza, F. J. Am. Chem. Soc. 1999, 121, 5961. (c) Anson, M. S.; Mirza, A. R.; Touks, L.; Williams, J. M. J. Tetrahedron Lett. 1999, 40, 7147. (d) Davis, M. E. Chemtec 1992, 498. (e) Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hauson, B. E. Nature 1989, 339, 454.
    • (1989) Nature , vol.339 , pp. 454
    • Arhancet, J.P.1    Davis, M.E.2    Merola, J.S.3    Hauson, B.E.4
  • 49
    • 0037685963 scopus 로고    scopus 로고
    • note
    • 2O-NaI system dispersed on chromatography silica gel prepared by simple mixing both reagents in acetonitrile followed by complete removal of the solvent.
  • 51
    • 0038361987 scopus 로고    scopus 로고
    • note
    • 2 system could be easily removed by filtration.
  • 52
    • 0000242844 scopus 로고
    • It is known (Iqbal, Z.; Kackson, A. H.; Nagaraja Rao, K. R. Tetrahedron Lett. 1988, 29, 2577) that Michael addition of 3-methylindole involves attack at the indole 3-position to form 3,3-disubstituted derivative, which undergoes migration to the 2-position of 3-oxoalkyl moiety.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2577
    • Iqbal, Z.1    Kackson, A.H.2    Nagaraja Rao, K.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.