메뉴 건너뛰기




Volumn 8, Issue 24, 2006, Pages 5661-5664

A general method for the catalytic nazarov cyclization of heteroaromatic compounds

Author keywords

[No Author keywords available]

Indexed keywords


EID: 33845997763     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062403v     Document Type: Article
Times cited : (131)

References (42)
  • 18
    • 0025125371 scopus 로고
    • For cyclizations of indole substrates, see: a
    • For cyclizations of indole substrates, see: (a) Bergman, J.; Venemalm, L. Tetrahedron 1990, 46, 6067.
    • (1990) Tetrahedron , vol.46 , pp. 6067
    • Bergman, J.1    Venemalm, L.2
  • 21
    • 0026718606 scopus 로고    scopus 로고
    • For cyclizations of thiophene substrates, see: (a) Kang, K.; Kim, S.; Lee, J.; U, J. Tetrahedron Lett. 1992, 33, 3495.
    • For cyclizations of thiophene substrates, see: (a) Kang, K.; Kim, S.; Lee, J.; U, J. Tetrahedron Lett. 1992, 33, 3495.
  • 24
    • 30944433040 scopus 로고    scopus 로고
    • For cyclizations of pyrrole substrates, see: a
    • For cyclizations of pyrrole substrates, see: (a) Song, C.; Knight, D.; Whatton, M. Org. Lett. 2005, 8, 163.
    • (2005) Org. Lett , vol.8 , pp. 163
    • Song, C.1    Knight, D.2    Whatton, M.3
  • 25
    • 0026718606 scopus 로고    scopus 로고
    • Kang, K.; Kim, S.; Lee, J.; U. J. Tetrahedron Lett. 1992, 33, 3495.
    • (b) Kang, K.; Kim, S.; Lee, J.; U. J. Tetrahedron Lett. 1992, 33, 3495.
  • 26
    • 84985206407 scopus 로고
    • For cyclizations of a benzofuran substrate, see
    • For cyclizations of a benzofuran substrate, see: Grant, H. J. Heterocycl. Chem. 1978, 15, 1235.
    • (1978) J. Heterocycl. Chem , vol.15 , pp. 1235
    • Grant, H.1
  • 28
    • 33846022464 scopus 로고    scopus 로고
    • E/Z isomerization takes place under the reaction conditions.
    • E/Z isomerization takes place under the reaction conditions.
  • 29
    • 33845972375 scopus 로고    scopus 로고
    • Upon Lewis acid activation of heteroaryl vinyl ketones, a pentadienyl cation is created. This extended π-system includes two p-orbitals of an aromatic ring, and although it will adopt conformations in which the aromatic system is decoupled from the companion allyl cation, overlap of all five p-orbitals must occur when the system cyclizes, so orbital symmetry should be conserved
    • Upon Lewis acid activation of heteroaryl vinyl ketones, a pentadienyl cation is created. This extended π-system includes two p-orbitals of an aromatic ring, and although it will adopt conformations in which the aromatic system is decoupled from the companion allyl cation, overlap of all five p-orbitals must occur when the system cyclizes, so orbital symmetry should be conserved.
  • 33
    • 0034122674 scopus 로고    scopus 로고
    • For reactions in which lithium perchlorate acts as a Lewis acidic catalyst, see the following review: Sankararaman, S.; Nesakumar, J. E. Eur. J. Org. Chem. 2000, 2003.
    • For reactions in which lithium perchlorate acts as a Lewis acidic catalyst, see the following review: Sankararaman, S.; Nesakumar, J. E. Eur. J. Org. Chem. 2000, 2003.
  • 34
    • 0028357606 scopus 로고
    • For accounts of scandium perchlorate catalysis, see: a
    • For accounts of scandium perchlorate catalysis, see: (a) Hachiya, I.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 3319.
    • (1994) Tetrahedron Lett , vol.35 , pp. 3319
    • Hachiya, I.1    Kobayashi, S.2
  • 37
    • 33846020152 scopus 로고    scopus 로고
    • 3CN, 80 °C, 3.5 h
    • 3CN, 80 °C, 3.5 h
  • 40
    • 0035814327 scopus 로고    scopus 로고
    • Asymmetric catalysis of a number of reactions using chiral Lewis acidic scandium complexes has been fruitful: (a) Evans, D, Sweeney, Z, Rovis, T, Tedrow, J. J. Am. Chem. Soc. 2001, 123, 12095
    • Asymmetric catalysis of a number of reactions using chiral Lewis acidic scandium complexes has been fruitful: (a) Evans, D.; Sweeney, Z.; Rovis, T.; Tedrow, J. J. Am. Chem. Soc. 2001, 123, 12095.
  • 42
    • 3543126652 scopus 로고    scopus 로고
    • For a study of Nazarov cyclization using chiral scandium complexes, see: c
    • For a study of Nazarov cyclization using chiral scandium complexes, see: (c) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 9544
    • Liang, G.1    Trauner, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.