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Volumn 10, Issue 23, 2008, Pages 5445-5448

Synthesis of spiroacetal enol ethers by oxidative activation of furan derivatives

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EID: 61349195809     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802138t     Document Type: Article
Times cited : (34)

References (65)
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    • Katritzky, A. R, Eds, Academic Press: San Diego
    • (a) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Eds.; Academic Press: San Diego, 1982; Vol. 30, pp 167-238.
    • (1982) Advances in Heterocyclic Chemistry , vol.30 , pp. 167-238
    • Dean, F.M.1
  • 2
    • 61349153455 scopus 로고
    • Katritzky, A. R, Ed, Academic Press: San Diego
    • (b) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1982; Vol. 30, pp 237-344.
    • (1982) In Advances in Heterocyclic Chemistry , vol.30 , pp. 237-344
    • Dean, F.M.1
  • 10
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    • Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114.
    • (b) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114.
  • 45
    • 33847289199 scopus 로고    scopus 로고
    • Wensley, A. M.; Hardy, A. O.; Gonsalves, K. M.; Koviach, J. L Tetrahedron Lett. 2007, 48, 2431-2434. See also ref 9c, e, f.
    • (f) Wensley, A. M.; Hardy, A. O.; Gonsalves, K. M.; Koviach, J. L Tetrahedron Lett. 2007, 48, 2431-2434. See also ref 9c, e, f.
  • 47
    • 61349114115 scopus 로고    scopus 로고
    • E.g, ferrocenium hexafluorophosphate, iron(III) nitrate, tetracyanoethylene, bis(acetoxy)iodobenzene, bis(trifluoroacetoxy)iodobenzene, cerium(IV) ammonium nitrate
    • E.g., ferrocenium hexafluorophosphate, iron(III) nitrate, tetracyanoethylene, bis(acetoxy)iodobenzene, bis(trifluoroacetoxy)iodobenzene, cerium(IV) ammonium nitrate.
  • 48
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    • 8c
    • 8c
  • 51
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    • First preparation: Armitage, J. B.; Cook, C. L.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C J. Chem. Soc. 1952, 1998-2005.
    • First preparation: Armitage, J. B.; Cook, C. L.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C J. Chem. Soc. 1952, 1998-2005.
  • 53
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    • In the 1H NMR spectrum of the crude product, the components 10, 19-OTBS, and 20 were present in a ratio of 50:40:10
    • 1H NMR spectrum of the crude product, the components 10, 19-OTBS, and 20 were present in a ratio of 50:40:10.
  • 59
    • 11944249437 scopus 로고    scopus 로고
    • The influence of allylic alkoxy groups on the stereoselectivity of alkene dihydroxylation is reviewed in: Cha, J. K, Kim, N.-S. Chem. Rev. 1995, 95, 1761-1795
    • The influence of allylic alkoxy groups on the stereoselectivity of alkene dihydroxylation is reviewed in: Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761-1795.
  • 60
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    • CCDC 697832 and 697833 contain crystallographic data for this paper (for compounds cis-Z-9 and cis-Z-21, respectively). These can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.cede.cam.ac.uk/data_request/cif.
    • CCDC 697832 and 697833 contain crystallographic data for this paper (for compounds cis-Z-9 and cis-Z-21, respectively). These can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.cede.cam.ac.uk/data_request/cif.
  • 61
    • 61349087795 scopus 로고    scopus 로고
    • 4) 1.45-1.70 and 1.84-2.00 (6 H, 2 × m), 1.90. 1.93 and 1.98 (3 × 3 H, 3 × s), 3.63-3.69 and 3.81-3.88 (2 × 1 H, 2 × m), 4.42* (1 H, app. s), 4.98* (1 H, d, J 4.7 Hz), 5.82* (1 H, poorly resolved dd, J 4.7. 1.8 Hz).
    • 4) 1.45-1.70 and 1.84-2.00 (6 H, 2 × m), 1.90. 1.93 and 1.98 (3 × 3 H, 3 × s), 3.63-3.69 and 3.81-3.88 (2 × 1 H, 2 × m), 4.42* (1 H, app. s), 4.98* (1 H, d, J 4.7 Hz), 5.82* (1 H, poorly resolved dd, J 4.7. 1.8 Hz).
  • 62
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    • 1H coupling constants in cyclopentanes, see: Constantino, M. G.; da Silva, G. V. J. Tetrahedron 1998, 54, 11363-11374.
    • 1H coupling constants in cyclopentanes, see: Constantino, M. G.; da Silva, G. V. J. Tetrahedron 1998, 54, 11363-11374.
  • 63
    • 61349101267 scopus 로고    scopus 로고
    • 21 by conversion of the diacetate into the corresponding alkene (i.e., Z-7) and comparison of data with those from an authentic sample.
    • 21 by conversion of the diacetate into the corresponding alkene (i.e., Z-7) and comparison of data with those from an authentic sample.


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