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Volumn 8, Issue 10, 2006, Pages 2147-2150

1,2-Bisanionic coupling approach to 2,3-disubstituted cyclopentenols and cyclopentenones

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EID: 33744765865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060654y     Document Type: Article
Times cited : (8)

References (32)
  • 1
    • 0035053973 scopus 로고    scopus 로고
    • Representative examples: (a) for prostaglandins, see: Straus, D. S.: Glass, C. K. Med. Res. Rev. 2001, 21, 185-210.
    • (2001) Med. Res. Rev. , vol.21 , pp. 185-210
    • Straus, D.S.1    Glass, C.K.2
  • 6
    • 0035900475 scopus 로고    scopus 로고
    • and references therein
    • (b) Trost, B. M.; Pinkerton, A. B. J. Org. Chem. 2001, 66, 7714-7722 and references therein.
    • (2001) J. Org. Chem. , vol.66 , pp. 7714-7722
    • Trost, B.M.1    Pinkerton, A.B.2
  • 11
    • 0000661691 scopus 로고
    • Adams, R., Ed.; Wiley: New York
    • Jones, R. G.; Gilman, H. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1951; Vol VI, pp 339-366.
    • (1951) Organic Reactions , vol.6 , pp. 339-366
    • Jones, R.G.1    Gilman, H.2
  • 12
    • 33744761233 scopus 로고    scopus 로고
    • note
    • Introduction of a protecting group was necessary in light of the prospected reactions of 2 with aliphatic halides.
  • 14
    • 0037503118 scopus 로고    scopus 로고
    • Rappoport, Z., Marek, I., Eds.; Wiley: New York
    • (b) The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: New York, 2004.
    • (2004) The Chemistry of Organolithium Compounds
  • 22
    • 33744760268 scopus 로고    scopus 로고
    • note
    • Easily available in four steps from commercial 1,3-cyclopentanedione, as depicted in Scheme 2.
  • 25
    • 33744761903 scopus 로고    scopus 로고
    • note
    • 2 (30 equiv), pentane, 5 h, room temperature; 85% overall yield.
  • 29
    • 33744756089 scopus 로고    scopus 로고
    • note
    • In contrast to 1-lithio-2-bromocyclopentene which is relatively stable up to 25 °C, 1-lithio-2-bromocyclohexene is reported to lose LiBr even at ≤ 120 °C, hampering the extension of this methodology to 1,2- dihalocyclohexenes.
  • 30
    • 84957159009 scopus 로고
    • For studies on the stability of different 1-lithio-2-halocycloalkenes, see: (a) Wittig, G.; Mayer, U. Chem. Ber. 1963, 96, 329-341.
    • (1963) Chem. Ber. , vol.96 , pp. 329-341
    • Wittig, G.1    Mayer, U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.