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Volumn 10, Issue 18, 2008, Pages 4073-4076

Interrupting the Nazarov cyclization with indoles

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PROTON;

EID: 55949101070     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801587u     Document Type: Article
Times cited : (42)

References (38)
  • 4
    • 0001992172 scopus 로고
    • For reviews of the Nazarov reaction, see: a, Paquette, L. A, Ed, John Wiley & Sons, Inc, New York
    • For reviews of the Nazarov reaction, see: (a) Habermas, K. L.; Denmark, S.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1994; Vol. 45, pp 1-158.
    • (1994) Organic Reactions , vol.45 , pp. 1-158
    • Habermas, K.L.1    Denmark, S.2    Jones, T.K.3
  • 5
  • 8
    • 20644435783 scopus 로고    scopus 로고
    • A Eur
    • (e) Tius, M. A Eur. J. Org. Chem. 2005, 2193-2206.
    • (2005) J. Org. Chem , pp. 2193-2206
    • Tius, M.1
  • 9
    • 0141520491 scopus 로고    scopus 로고
    • For recent examples of the Nazarov reaction, see: a
    • For recent examples of the Nazarov reaction, see: (a) Li, W-D. Z.: Wang, Y-Q. Org. Lett. 2003, 5, 2931-2934.
    • (2003) Org. Lett , vol.5 , pp. 2931-2934
    • Li, W.-D.Z.1    Wang, Y.-Q.2
  • 24
    • 27144484967 scopus 로고    scopus 로고
    • Giese, S.; Mazzola, R. D., Jr.; Amann, C. M.; Arif, A. M.; West, F. G. Angew. Chem., Int. Ed. 2005, 44, 6546-6549.
    • (e) Giese, S.; Mazzola, R. D., Jr.; Amann, C. M.; Arif, A. M.; West, F. G. Angew. Chem., Int. Ed. 2005, 44, 6546-6549.
  • 32
    • 41049108081 scopus 로고    scopus 로고
    • This recent paper by the West group describes the capture of pentadienyl carbocations by electron-rich aromatics and is conceptually related to the present work
    • Rieder, C. J.; Fradette, R. J.; West, F. G. Chem. Commun. 2008, 1572-1574. This recent paper by the West group describes the capture of pentadienyl carbocations by electron-rich aromatics and is conceptually related to the present work.
    • (2008) Chem. Commun , pp. 1572-1574
    • Rieder, C.J.1    Fradette, R.J.2    West, F.G.3
  • 33
    • 61349125853 scopus 로고    scopus 로고
    • To the best of our knowledge, this type of bond cleavage followed by rearrangement has not been previously reported
    • To the best of our knowledge, this type of bond cleavage followed by rearrangement has not been previously reported.
  • 34
    • 61349157037 scopus 로고    scopus 로고
    • The step that converts 3 to 14 does not lead to allenyl vinyl ketone, indicating that there is no competition with an alkyne-allene isomerization process.
    • The step that converts 3 to 14 does not lead to allenyl vinyl ketone, indicating that there is no competition with an alkyne-allene isomerization process.
  • 36
    • 61349157639 scopus 로고    scopus 로고
    • 3 would be expected to preserve a trimethylsilyl enol ether (cf. 14)
    • The trimethylsilyl group is presumably lost after indole trapping but before workup, may serve as the silylophile
    • 3 would be expected to preserve a trimethylsilyl enol ether (cf. 14). Adventitious water may serve as the silylophile.
    • Adventitious water


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.