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Volumn 5, Issue 9, 2003, Pages 1567-1569

Regio- and stereoselective ruthenium-catalyzed hydrovinylation of 1,3-dienes: Application to the generation of a 20(S) steroidal side chain

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; COLECALCIFEROL DERIVATIVE; CYCLOALKENE; ESTRONE DERIVATIVE; ETHYLENE; RO 26 9228; RUTHENIUM; RUTHENIUM COMPLEX; STEROID; VINYL DERIVATIVE; ETHYLENE DERIVATIVE; ORGANOMETALLIC COMPOUND;

EID: 0041764978     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030031+     Document Type: Article
Times cited : (47)

References (34)
  • 3
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    • (1991) Science , vol.254 , pp. 1471-1477
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  • 19
    • 0141714666 scopus 로고    scopus 로고
    • note
    • Neither 1,4-diphenyl-1,3-butadiene or 2,5-dimethyl-2,4-hexadiene reacted with ethylene in the presence of either 1 or 2.
  • 20
    • 0141714652 scopus 로고    scopus 로고
    • note
    • Isomerization (over longer reaction periods) is observed with both catalysts 1 and 2. Thus, at least for catalyst 1, this isomerization cannot be attributed to the presence of acid.
  • 21
    • 0017865325 scopus 로고
    • Both the 20(S)- and 20(R)-isomers of the methyl ether corresponding to benzyl ether 6 have been previously prepared. The close similarity of their literature NMR spectral data does not allow for an unambiguous assignment. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435-3443.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3435-3443
    • Trost, B.M.1    Verhoeven, T.R.2
  • 22
    • 0009607379 scopus 로고
    • Formation of γ-lactones from 4-penten-1-ols or δ-lactones from 5-hexen-1-ols via oxidation with chromium reagents has been previously reported. (a) Chakraborty, T. K.; Chandrasekaran, S. Tetrahedron Lett. 1984, 25, 2895-2896. (b) Schlecht, M. F.; Kim, H. Tetrahedron Lett. 1985, 26, 127-130. (c) Rathore, R.; Vankar, P. S.; Chandrasekaran, S. Tetrahedron Lett. 1986, 27, 4079-4082.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2895-2896
    • Chakraborty, T.K.1    Chandrasekaran, S.2
  • 23
    • 0002674996 scopus 로고
    • Formation of γ-lactones from 4-penten-1-ols or δ-lactones from 5-hexen-1-ols via oxidation with chromium reagents has been previously reported. (a) Chakraborty, T. K.; Chandrasekaran, S. Tetrahedron Lett. 1984, 25, 2895-2896. (b) Schlecht, M. F.; Kim, H. Tetrahedron Lett. 1985, 26, 127-130. (c) Rathore, R.; Vankar, P. S.; Chandrasekaran, S. Tetrahedron Lett. 1986, 27, 4079-4082.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 127-130
    • Schlecht, M.F.1    Kim, H.2
  • 24
    • 0003985845 scopus 로고
    • Formation of γ-lactones from 4-penten-1-ols or δ-lactones from 5-hexen-1-ols via oxidation with chromium reagents has been previously reported. (a) Chakraborty, T. K.; Chandrasekaran, S. Tetrahedron Lett. 1984, 25, 2895-2896. (b) Schlecht, M. F.; Kim, H. Tetrahedron Lett. 1985, 26, 127-130. (c) Rathore, R.; Vankar, P. S.; Chandrasekaran, S. Tetrahedron Lett. 1986, 27, 4079-4082.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4079-4082
    • Rathore, R.1    Vankar, P.S.2    Chandrasekaran, S.3
  • 31
    • 11944270778 scopus 로고
    • For a review, see: Gui-Dong, Z.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952. For a more recent synthesis, see: Yan, J.; Herndon, J. W. J. Org. Chem. 1998, 63, 2325-2331 and references therein.
    • (1995) Chem. Rev. , vol.95 , pp. 1877-1952
    • Gui-Dong, Z.1    Okamura, W.H.2
  • 32
    • 0001482246 scopus 로고    scopus 로고
    • and references therein
    • For a review, see: Gui-Dong, Z.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952. For a more recent synthesis, see: Yan, J.; Herndon, J. W. J. Org. Chem. 1998, 63, 2325-2331 and references therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 2325-2331
    • Yan, J.1    Herndon, J.W.2
  • 33
    • 0034835668 scopus 로고    scopus 로고
    • 3 precursors have been prepared by ozonolytic degradation of ergocalciferol, followed by a base-catalyzed epimerization and separation of the 20(R)- and 20(S)-diastereomers: Hijikuro, D. T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722. For a route to the 20(S) side chain that uses stoichiometric palladium, see ref 8.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3716-3722
    • Hijikuro, D.T.1    Takahashi, T.2
  • 34
    • 0141826073 scopus 로고    scopus 로고
    • note
    • Notably, the Ru-H species 10 has been proposed as an intermediate in the coupling of alkynes with ethylene using catalyst 1 (see ref 5a).


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