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Volumn 52, Issue 14, 2011, Pages 1709-1712

Ti(III)-mediated opening of 2,3-epoxy alcohols to build five-membered carbocycles with multiple chiral centres

Author keywords

Carbocyclization; Epoxide opening; Free radicals; Iridoids; Sharpless kinetic resolution; Ti(III)

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; CARBOCYCLE DERIVATIVE; EPOXIDE; NATURAL PRODUCT; TITANIUM; UNCLASSIFIED DRUG;

EID: 79952446518     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.001     Document Type: Article
Times cited : (6)

References (56)
  • 5
    • 0001562822 scopus 로고
    • D.J. Hart Science 223 1984 883 887
    • (1984) Science , vol.223 , pp. 883-887
    • Hart, D.J.1
  • 28
    • 12044258371 scopus 로고
    • For the preparation of highly functionalized five-membered carbocycles, even though a wide variety of methods were found, select methods are mentioned here. For example: transformation of carbohydrates to cyclopentanes, see: R.J. Ferrier, and S. Middleton Chem. Rev. 93 1993 2779 2831
    • (1993) Chem. Rev. , vol.93 , pp. 2779-2831
    • Ferrier, R.J.1    Middleton, S.2
  • 34
    • 77954117148 scopus 로고    scopus 로고
    • For transition metal mediated C-C bond forming reactions, see: K. Takahashi, and T. Honda Org. Lett. 12 2010 3026 3029 and the references cited therein.
    • (2010) Org. Lett. , vol.12 , pp. 3026-3029
    • Takahashi, K.1    Honda, T.2
  • 35
    • 0037884930 scopus 로고    scopus 로고
    • For intramolecular [3+2] cycloaddition reactions, see: H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
    • (2003) Chem. Rev. , vol.103 , pp. 1151-1196
    • Reissig, H.-U.1    Zimmer, R.2
  • 53
    • 79952443274 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. Purification by using standard silica gel column chromatography (22-28% ethyl acetate in petroleum ether eluant) afforded the five-membered carbocycles 7A-D.
  • 54
    • 79952453668 scopus 로고    scopus 로고
    • note
    • 3)
  • 56
    • 79952453192 scopus 로고    scopus 로고
    • note
    • Consistent pattern of a cis-junction has been observed in the formation of five-membered targets and a trans-junction in six-membered targets during our previous Ti(III) mediated epoxide opening reactions. See: Refs. 3c-e and 4a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.