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Volumn , Issue 1, 2000, Pages 95-97

A new cycloisomerisation catalyst of enynes: One-step synthesis of 3,4- dialkylidenetetrahydrofurans from allyl propargyl ethers

Author keywords

Allyl propargyl ethers; Catalysis; Cycloisomerisation; Dialkylidenetetrahydrofurans; Ruthenium

Indexed keywords

ACETIC ACID; ALCOHOL; ETHER DERIVATIVE; RUTHENIUM; TETRAHYDROFURAN DERIVATIVE;

EID: 0343819803     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (13)

References (20)
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    • Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850-1852. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781-1783. Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268-4278; Trost, B. M.; Haffner, C. D.; Jebaratnam, D. J.; Krische, M. J.; Thomas, A. P. J. Am. Chem. Soc. 1999, 121, 6183-6192. Trost, B. M.; Krische, M. J. J. Am. Chem. Soc. 1999, 121, 6131-6141.
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    • Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850-1852. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781-1783. Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268-4278; Trost, B. M.; Haffner, C. D.; Jebaratnam, D. J.; Krische, M. J.; Thomas, A. P. J. Am. Chem. Soc. 1999, 121, 6183-6192. Trost, B. M.; Krische, M. J. J. Am. Chem. Soc. 1999, 121, 6131-6141.
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    • Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850-1852. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781-1783. Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268-4278; Trost, B. M.; Haffner, C. D.; Jebaratnam, D. J.; Krische, M. J.; Thomas, A. P. J. Am. Chem. Soc. 1999, 121, 6183-6192. Trost, B. M.; Krische, M. J. J. Am. Chem. Soc. 1999, 121, 6131-6141.
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    • Trost, B.M.1    Haffner, C.D.2    Jebaratnam, D.J.3    Krische, M.J.4    Thomas, A.P.5
  • 13
    • 0033532937 scopus 로고    scopus 로고
    • Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850-1852. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781-1783. Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268-4278; Trost, B. M.; Haffner, C. D.; Jebaratnam, D. J.; Krische, M. J.; Thomas, A. P. J. Am. Chem. Soc. 1999, 121, 6183-6192. Trost, B. M.; Krische, M. J. J. Am. Chem. Soc. 1999, 121, 6131-6141.
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  • 16
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    • note
    • The allyl propargyl ethers 1 were conveniently prepared from the corresponding prop-2-yn-1-ols on successive treatment with NaH and allyl bromide in DMF at room temperature.
  • 17
    • 0343929564 scopus 로고    scopus 로고
    • note
    • endo), 7.23 (s, 1H, = CH(Ph)), 6.74 - 7.58 (m, 15H, Ph). NOE experiments for 5a, the irradiation at δ = 5.48 ppm leads to an increase of 21.5% of the signal at δ = 6.84 ppm, and for 5d, the irradiation at δ = 7.23 ppm leads to an increase of 11% of the signal at δ = 5.40 ppm.


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