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Volumn 9, Issue 16, 2007, Pages 3069-3072

Phosphine-catalyzed synthesis of highly functionalized coumarins

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; PHOSPHINE; PHOSPHINE DERIVATIVE;

EID: 34547957084     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071181d     Document Type: Article
Times cited : (160)

References (79)
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    • O'Kennedy, R, Thornes, R. D, Eds, John Wiley & Sons: New York
    • (a) Coumarins: Biology, Applications, and Mode of Action; O'Kennedy, R., Thornes, R. D., Eds.; John Wiley & Sons: New York, 1997.
    • (1997) Coumarins: Biology, Applications, and Mode of Action
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    • Zahradnik, M the Production and Application of Fluorescent Brightening Agents; Wiley: New York, 1982.
    • (a) Zahradnik, M the Production and Application of Fluorescent Brightening Agents; Wiley: New York, 1982.
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    • Reference 8g
    • (b) Reference 8g.
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    • 8e
    • (c) 8e.
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    • For an example of γ-selective intramolecular alkyne/alkene [3 + 2] cycloaddition, see: Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682.
    • For an example of γ-selective intramolecular alkyne/alkene [3 + 2] cycloaddition, see: Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682.
  • 65
    • 34547930435 scopus 로고    scopus 로고
    • Use of the common (peptide) coupling reagents [DCC, TCT, Hf(IV) salts, HBTU, HATU, and PyBroP] failed to provide the allenoate product. Presumably, the product allenoate is susceptible to nucleophilic attack by either a base present in the reaction medium or the byproducts derived from the coupling reagents. See the Supporting Information for details regarding the isolation and characterization of the product of N-hydroxybenzotriazole addition to the allenoate when using HBTU.
    • Use of the common (peptide) coupling reagents [DCC, TCT, Hf(IV) salts, HBTU, HATU, and PyBroP] failed to provide the allenoate product. Presumably, the product allenoate is susceptible to nucleophilic attack by either a base present in the reaction medium or the byproducts derived from the coupling reagents. See the Supporting Information for details regarding the isolation and characterization of the product of N-hydroxybenzotriazole addition to the allenoate when using HBTU.
  • 67
    • 34547937837 scopus 로고    scopus 로고
    • The connectivity and relative stereochemistry of this compound were assigned through NMR spectroscopic analyses. See the Supporting Information for details
    • The connectivity and relative stereochemistry of this compound were assigned through NMR spectroscopic analyses. See the Supporting Information for details.
  • 68
    • 34547933404 scopus 로고    scopus 로고
    • NOE analyses confirmed the trans stereochemistry of the [3 + 2] annulation product. See the Supporting Information for details.
    • NOE analyses confirmed the trans stereochemistry of the [3 + 2] annulation product. See the Supporting Information for details.
  • 69
    • 34547932351 scopus 로고    scopus 로고
    • See the Supporting Information for the syntheses of 1i and 1j
    • See the Supporting Information for the syntheses of 1i and 1j.
  • 70
    • 0000444401 scopus 로고
    • For reviews on the preparation and use of nitronates, see: a, Katritzky, A. R, Boulton, A. J, Eds, Academic: New York
    • For reviews on the preparation and use of nitronates, see: (a) Takaeuchi, Y.; Furusaki, F. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1977; Vol. 21, p 207.
    • (1977) Advances in Heterocyclic Chemistry , vol.21 , pp. 207
    • Takaeuchi, Y.1    Furusaki, F.2
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    • Döpp, H.; Döpp, D. In Modern der Organischen Chemie (Houben-Weyl), 4th ed.; Klamann, D., Hagemann, H., Eds.; Georg Thieme: Stuttgart, 1990; E14b/1, p 880.
    • (e) Döpp, H.; Döpp, D. In Modern der Organischen Chemie (Houben-Weyl), 4th ed.; Klamann, D., Hagemann, H., Eds.; Georg Thieme: Stuttgart, 1990; Vol. E14b/1, p 880.
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    • Crystallographic data for 4a, 5a, and 4d have been deposited with the Cambridge Crystallographic Data Centre as supplementary numbers CCDC 602367-602369. These data can be obtained online free of charge (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 lEZ, UK; fax: (+44) 1223-336-033; or deposit@ ccdc.cam.ac.uk).
    • Crystallographic data for 4a, 5a, and 4d have been deposited with the Cambridge Crystallographic Data Centre as supplementary numbers CCDC 602367-602369. These data can be obtained online free of charge (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 lEZ, UK; fax: (+44) 1223-336-033; or deposit@ ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.