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Volumn 38, Issue 7, 1997, Pages 1153-1156

Samarium(II) iodide mediated transformations of carbohydrate derived alkenyl iodides

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CYCLOPENTANE DERIVATIVE;

EID: 0031575646     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00012-9     Document Type: Article
Times cited : (40)

References (37)
  • 8
    • 12044258371 scopus 로고
    • 3. For a review on the conversion of carbohydrates to functionalized carbocycles see: Ferrier, R.J.; Midleton, S. Chem. Rev. 1993, 93, 2779-2831.
    • (1993) Chem. Rev. , vol.93 , pp. 2779-2831
    • Ferrier, R.J.1    Midleton, S.2
  • 9
    • 0028218744 scopus 로고
    • 2 mediated transformations of carbohydrates to carbocycles via an intramolecular coupling of an aldehyde carbonyl with an α,β - unsaturated ester see: (a) Enholm, E. J. ; Trivellas, A. Tetrahedron Lett. 1994, 35, 1627-1628.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1627-1628
    • Enholm, E.J.1    Trivellas, A.2
  • 13
    • 0000973977 scopus 로고
    • 3SnH mediated radical cyclizations of ωbromo-α,β-unsaturated ethyl esters, derived from D-ribonolactone, have been reported in the literature. See: Wilcox, C.S.; Thomasco, L.M. J. Org. Chem. 1985, 50, 546-547.
    • (1985) J. Org. Chem. , vol.50 , pp. 546-547
    • Wilcox, C.S.1    Thomasco, L.M.2
  • 14
    • 33847086035 scopus 로고
    • 2 reduction of alkyl halides to the corresponding alkanes was first demonstrated by Kagan. See: (a) Girard, P.; Namy, J.L.; Kagan, H.B. J. Am. Chem. Soc. 1980, 102, 2693 - 2698.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693-2698
    • Girard, P.1    Namy, J.L.2    Kagan, H.B.3
  • 16
    • 0011472960 scopus 로고    scopus 로고
    • 2 reactions of unsaturated halides see references 1a and 1c and references therein
    • 2 reactions of unsaturated halides see references 1a and 1c and references therein.
  • 21
    • 0011382263 scopus 로고    scopus 로고
    • Commercially available from Aldrich
    • 10. Commercially available from Aldrich.
  • 22
    • 0011429302 scopus 로고    scopus 로고
    • The purification of the 4a and 4b was complicated by the presence of tetrahydrofuran side products (formed by an intramolecular 1,4 - addition of the hydroxyl group onto the α, β-unsaturated ester)
    • 11. The purification of the 4a and 4b was complicated by the presence of tetrahydrofuran side products (formed by an intramolecular 1,4 - addition of the hydroxyl group onto the α, β-unsaturated ester).
  • 25
    • 0011382381 scopus 로고    scopus 로고
    • 13C NMR, FTIR, MS) are in agreement with the proposed structures. Yields refer to isolated yields of pure products
    • 13C NMR, FTIR, MS) are in agreement with the proposed structures. Yields refer to isolated yields of pure products.
  • 29
    • 0011382382 scopus 로고    scopus 로고
    • note
    • 4 and concd. The crude products were purified by flash column chromatography or by radial chromatography [Harrison Research Chromatotron, silica gel or adsorbosil plates] using a mixture of EtOAc and hexanes.
  • 30
    • 0011383211 scopus 로고    scopus 로고
    • 3SnH reactions
    • 3SnH reactions.
  • 31
    • 0011440260 scopus 로고    scopus 로고
    • The stereochemistry of the cyclization products was determined with the help of nOe experiments
    • 18. The stereochemistry of the cyclization products was determined with the help of nOe experiments.
  • 32
    • 0011383654 scopus 로고    scopus 로고
    • 1H NMR analysis of both the crude and purified products
    • 1H NMR analysis of both the crude and purified products.
  • 33
    • 0026016178 scopus 로고
    • 2 radical addition/reductive elimination sequence involving a simple aromatic bromide tethered to an allylic acetate has been reported. See: Inanaga, J.; Ujikawa, O.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 1737-1740.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1737-1740
    • Inanaga, J.1    Ujikawa, O.2    Yamaguchi, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.