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Volumn 73, Issue 7, 2008, Pages 2886-2889

Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; FLUORINATION; MICROWAVE IRRADIATION; SYNTHESIS (CHEMICAL);

EID: 41649118478     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800088y     Document Type: Article
Times cited : (64)

References (38)
  • 2
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    • Katritzky A. R, Ed, Academic Press: New York
    • (b) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky A. R., Ed.; Academic Press: New York, 1983; Vol. 31, pp 273-344.
    • (1983) Advances in Heterocyclic Chemistry , vol.31 , pp. 273-344
    • Dean, F.M.1
  • 3
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    • Nakanishi, K, Goto, T, Ito, S, Natori, S, Nozoe, S, Eds, Kodansha: Tokyo, Vols
    • (c) Nakanishi, K., Goto, T., Ito, S., Natori, S., Nozoe, S., Eds.; Natural Products Chemistry; Kodansha: Tokyo, 1974; Vols. 1-3.
    • (1974) Natural Products Chemistry , vol.1-3
  • 7
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    • and references cited therein
    • (d) Stauffer, F.; Neier, R. Org. Lett. 2000, 2, 3535-3537 and references cited therein.
    • (2000) Org. Lett , vol.2 , pp. 3535-3537
    • Stauffer, F.1    Neier, R.2
  • 8
    • 37349012130 scopus 로고    scopus 로고
    • For examples of substituted 3-fluorofurans, see: (a) Pomeisl, K, Cejka, J, Kvicala, J, Paleta, O. Eur. J. Org. Chem. 2007, 5917-5923
    • For examples of substituted 3-fluorofurans, see: (a) Pomeisl, K.; Cejka, J.; Kvicala, J.; Paleta, O. Eur. J. Org. Chem. 2007, 5917-5923.
  • 12
    • 33747237825 scopus 로고    scopus 로고
    • For general reviews, see: a, Blackwell: Oxford
    • For general reviews, see: (a) Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, 2006.
    • (2006) Organofluorine Chemistry
    • Uneyama, K.1
  • 16
    • 2942537776 scopus 로고    scopus 로고
    • For examples of 3,3-gem-difluoromethylenated nucleoacids, see: (e) Zhou, W, Gumina, G, Chong, Y, Wang, J, Schinazi, R. F, Chu, C. K. J. Med. Chem. 2004, 47, 3399-3408
    • For examples of 3,3-gem-difluoromethylenated nucleoacids, see: (e) Zhou, W.; Gumina, G.; Chong, Y.; Wang, J.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2004, 47, 3399-3408.
  • 20
    • 33646389572 scopus 로고    scopus 로고
    • For a review of gem-difluoroallenes, see: (a) Hammond, G. B. J. Fluorine Chem. 2006, 127, 476-488.
    • For a review of gem-difluoroallenes, see: (a) Hammond, G. B. J. Fluorine Chem. 2006, 127, 476-488.
  • 21
    • 33846627323 scopus 로고    scopus 로고
    • For synthesis of gem-difluorohomopropargyl alcohols, see: (b) Arimitsu, S.; Jacobsen, J. M.; Hammond, G. B. Tetrahedron Lett. 2007, 48, 1625-1627.
    • For synthesis of gem-difluorohomopropargyl alcohols, see: (b) Arimitsu, S.; Jacobsen, J. M.; Hammond, G. B. Tetrahedron Lett. 2007, 48, 1625-1627.
  • 25
    • 41649112161 scopus 로고    scopus 로고
    • See refs 3b and 5d
    • See refs 3b and 5d.
  • 30
    • 41649119037 scopus 로고    scopus 로고
    • The use of normal silica gel for isolation resulted in the decomposition of the benzyl ether group (entries 4 and 5, Table 2) and a difficult separation from byproducts entry 6, Table 2
    • The use of normal silica gel for isolation resulted in the decomposition of the benzyl ether group (entries 4 and 5, Table 2) and a difficult separation from byproducts (entry 6, Table 2).
  • 31
    • 7644241634 scopus 로고    scopus 로고
    • For reviews of the Suzuki-Miyaura cross-coupling, see: a
    • For reviews of the Suzuki-Miyaura cross-coupling, see: (a) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419-2440.
    • (2004) Synthesis , pp. 2419-2440
    • Bellina, F.1    Carpita, A.2    Rossi, R.3
  • 34
    • 41649094668 scopus 로고    scopus 로고
    • A similar base-mediated cyclization of gem-difluorohomopropargyl alcohol was reported. This report claimed that 3-fluoro-2,5-substituted furans were obtained via a 3-exo-tet cyclization. See ref 3d
    • A similar base-mediated cyclization of gem-difluorohomopropargyl alcohol was reported. This report claimed that 3-fluoro-2,5-substituted furans were obtained via a 3-exo-tet cyclization. See ref 3d.
  • 36
    • 0001592343 scopus 로고
    • and references cited therein. A cyclic iodonium ion intermediate has been proposed. See
    • A cyclic iodonium ion intermediate has been proposed. See: Barluenga, J.; Rodríguez, M. A.; Campos, P. J. J. Org. Chem. 1990, 55, 3104-3106 and references cited therein.
    • (1990) J. Org. Chem , vol.55 , pp. 3104-3106
    • Barluenga, J.1    Rodríguez, M.A.2    Campos, P.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.