메뉴 건너뛰기




Volumn , Issue 8, 2005, Pages 1199-1222

A journey across recent advances in catalytic and stereoselective alkylation of indoles

Author keywords

Alkylations; Asymmetric catalysis; Electrophilic aromatic substitutions; Indoles; Lewis acids

Indexed keywords

1,3 BISINDOLYLKETONE DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; AROMATIC COMPOUND; BROMINE DERIVATIVE; EPOXIDE; INDIUM; INDOLE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; PALLADIUM; PYRAN DERIVATIVE; THIOESTER; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 19944413632     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865210     Document Type: Review
Times cited : (392)

References (183)
  • 10
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: San Diego
    • (b) Sundberg, R. J. In Indoles; Academic Press: San Diego, 1996.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 58
    • 0000405865 scopus 로고
    • The intramolecular aromatic friedel-crafts reaction
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford
    • Heaney, H. The Intramolecular Aromatic Friedel-Crafts Reaction, In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991.
    • (1991) Comprehensive Organic Synthesis
    • Heaney, H.1
  • 86
    • 19944378471 scopus 로고    scopus 로고
    • note
    • Mass flow rate of reactant for mass of catalyst utilized in the reactor.
  • 87
    • 0035905145 scopus 로고    scopus 로고
    • For representative examples of indole alkylation through ring opening of epoxides mediated by a stoichiometric amount of LA see: (a) Kato, K.; Ono, M.; Akita, H. Tetrahedron 2001, 57, 10055.
    • (2001) Tetrahedron , vol.57 , pp. 10055
    • Kato, K.1    Ono, M.2    Akita, H.3
  • 94
    • 19944413361 scopus 로고    scopus 로고
    • note
    • In fact, electronic properties of aromatic epoxides are known to drive the ring-opening with indoles at the benzylic position.
  • 97
    • 19944381568 scopus 로고    scopus 로고
    • note
    • Aliphatic epoxides were not found suitable candidates for the present catalytic indole alkylation giving the β-indolyl alcohols in poor yield as well as regioselectivity.
  • 98
    • 0001726667 scopus 로고    scopus 로고
    • Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Chap. 21, and references cited therein
    • Itsuno, S. In Lewis Acids in Organic Synthesis, Vol. 2; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 21, 945; and references cited therein.
    • (2000) Lewis Acids in Organic Synthesis , vol.2 , pp. 945
    • Itsuno, S.1
  • 101
    • 0001001230 scopus 로고    scopus 로고
    • By an analogous synthetic procedure polymer-supported lanthanide(III) catalysts were also prepared see: Yu, L.; Chen, D.; Li, J.; Wang, P. G. J. Org. Chem. 1997, 62, 3575.
    • (1997) J. Org. Chem. , vol.62 , pp. 3575
    • Yu, L.1    Chen, D.2    Li, J.3    Wang, P.G.4
  • 129
    • 19944387350 scopus 로고    scopus 로고
    • note
    • 2, and Tol-BINAP-CuOTf led to the formation of 50 in significant yields. However the enantioselectivity recorded was poor with ee ranging from 0-36%.
  • 131
    • 0037015425 scopus 로고    scopus 로고
    • Pybox-Sc(III) complexes were already employed as chiral Lewis acids in numerous asymmetric transformation: see (a) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375.
    • (2002) Org. Lett. , vol.4 , pp. 3375
    • Evans, D.A.1    Masse, C.E.2    Wu, J.3
  • 135
    • 0034807741 scopus 로고    scopus 로고
    • For related asymmetric organo-catalyzed FC alkylation of aromatic compounds see: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4370
    • Paras, N.A.1    MacMillan, D.W.C.2
  • 137
    • 5444271233 scopus 로고    scopus 로고
    • Theoretical exploration of the stereoselective organocatalyzed FC alkylation of indoles was recently performed: Gordillo, R.; Carter, J.; Houk, K. N. Adv. Synth. Catal. 2004, 346, 1175.
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1175
    • Gordillo, R.1    Carter, J.2    Houk, K.N.3
  • 140
    • 0033615304 scopus 로고    scopus 로고
    • Selected examples of [SalenAlCl]-catalyzed asymmetric organic transformations: (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8959
    • Myers, J.K.1    Jacobsen, E.N.2
  • 147
    • 0035128046 scopus 로고    scopus 로고
    • and references cited therein
    • (h) Chiral aluminum-Schiff base complexes have been fully spectroscopically as well as crystallograpically characterized: Atwood, D. A.; Harvey, M. J. Chem. Rev. 2001, 101, 37; and references cited therein.
    • (2001) Chem. Rev. , vol.101 , pp. 37
    • Atwood, D.A.1    Harvey, M.J.2
  • 152
    • 0034603013 scopus 로고    scopus 로고
    • For recent representative examples of computational investigations of metallo-salen complex geometries and their effects on enantioselective transformations see: (a) Cavallo, L.; Jacobsen, H. Angew. Chem. Int. Ed. 2000, 39, 589.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 589
    • Cavallo, L.1    Jacobsen, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.