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Volumn 120, Issue 22, 1998, Pages 5587-5588

Ruthenium-catalyzed β-allyl elimination leading to selective cleavage of a carbon-carbon bond in homoallyl alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; RUTHENIUM;

EID: 18244427166     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980714y     Document Type: Article
Times cited : (156)

References (32)
  • 1
    • 0003625966 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K.
    • Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Hegedus, L.S.1
  • 2
    • 0009679346 scopus 로고
    • For reviews, see: (a) Bishop, K. C. Chem. Rev. 1976, 76, 461.
    • (1976) Chem. Rev. , vol.76 , pp. 461
    • Bishop, K.C.1
  • 26
    • 0002446724 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, U.K.
    • Addition of allylorganometallics to carbonyl compounds, see: Roush, W. R. In Comprehensive Organic Synthesis: Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 2, pp 1-53.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1-53
    • Roush, W.R.1
  • 28
    • 85034195310 scopus 로고    scopus 로고
    • In the reaction of 1d, a small amount (0.36 mmol) of propene was generated from allyl acetate (30 mmol) together with isobutene (1.68 mmol, 42%) from 1d
    • In the reaction of 1d, a small amount (0.36 mmol) of propene was generated from allyl acetate (30 mmol) together with isobutene (1.68 mmol, 42%) from 1d.
  • 29
    • 33748407735 scopus 로고
    • In addition, carbon monoxide can be replaced by maleic anhydride (yield of 1a, 65%; see the Supporting Information). These results indicate that carbon monoxide and maleic anhydride may coordinate to an active ruthenium center and promote the reductive elimination of propene from a (hydrido)(allyl)ruthenium intermediate, as well as control the electronic condition of an active ruthenium center
    • 2 (Stephenson, T. A.; Wilkinson, G. J. Inorg. Nucl. Chem. 1966, 28, 945). In addition, carbon monoxide can be replaced by maleic anhydride (yield of 1a, 65%; see the Supporting Information). These results indicate that carbon monoxide and maleic anhydride may coordinate to an active ruthenium center and promote the reductive elimination of propene from a (hydrido)(allyl)ruthenium intermediate, as well as control the electronic condition of an active ruthenium center.
    • (1966) J. Inorg. Nucl. Chem. , vol.28 , pp. 945
    • Stephenson, T.A.1    Wilkinson, G.2
  • 31
    • 0011033370 scopus 로고
    • The thermal ring-opening reaction (retro-ene reaction) of 2-vinyl-cyclohexanols is generally carried out in the vapor phase at ca. 500 °C. Marvell, E. N.; Rusay, R. J. Org. Chem. 1977, 42, 3336.
    • (1977) J. Org. Chem. , vol.42 , pp. 3336
    • Marvell, E.N.1    Rusay, R.2
  • 32
    • 85034163659 scopus 로고    scopus 로고
    • note
    • 3 catalyst and an excess amount of allyl acetate in THF gave the transfer-allylated product, (E)-1-phenyl-2-buten-1-one (8a) and 3-methyl-1-phenylbut-2-en-1-one (9a) in yields of 68 and 35%, respectively (eq 8). Of course, no reaction occurred in the absence of 1a or 1d, even in the presence of allyl acetate Matrix equation presented.


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