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Volumn 27, Issue 15, 2008, Pages 3866-3878

Acidic ruthenium PNNP complexes of non-enolized 1,3-dicarbonyl compounds as catalysts for asymmetric michael addition

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CATALYSIS; RUTHENIUM;

EID: 50549103280     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800197y     Document Type: Article
Times cited : (40)

References (76)
  • 26
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    • A complex claimed to contain non-enolized N,N′- diphenylmalonamide is probably a Ru(III) enolato complex, as it has been reported to be paramagnetic: (b) Blum, J.; Fisher, A.; Greener, E. Tetrahedron 1973, 29, 1073.
    • A complex claimed to contain non-enolized N,N′- diphenylmalonamide is probably a Ru(III) enolato complex, as it has been reported to be paramagnetic: (b) Blum, J.; Fisher, A.; Greener, E. Tetrahedron 1973, 29, 1073.
  • 27
    • 0002150904 scopus 로고    scopus 로고
    • For an overview on different coordination modes of 1,3-dicarbonyl ligands and examples of Ni(II), Co(II), Cu(II), and Zn(II) complexes with acetylacetone, malonate, and malonamide, see: (c) Kawaguchi, S. Coord. Chem. Rev. 1986, 70, 51.
    • For an overview on different coordination modes of 1,3-dicarbonyl ligands and examples of Ni(II), Co(II), Cu(II), and Zn(II) complexes with acetylacetone, malonate, and malonamide, see: (c) Kawaguchi, S. Coord. Chem. Rev. 1986, 70, 51.
  • 33
    • 0006066316 scopus 로고    scopus 로고
    • +: Arnett, E. M.; Wu, C. Y. J. Am. Chem. Soc. 1960, 82, 4999.
    • +: Arnett, E. M.; Wu, C. Y. J. Am. Chem. Soc. 1960, 82, 4999.
  • 34
    • 50549104580 scopus 로고    scopus 로고
    • Containing the racemic PNNP ligand prepared from (rac)-trans-1,2- diaminocyclohexane.
    • Containing the racemic PNNP ligand prepared from (rac)-trans-1,2- diaminocyclohexane.
  • 37
    • 33746825962 scopus 로고    scopus 로고
    • Spohn, M.; Strahle, J.; Hiller, W. Z. Naturforsch. B. 1986, 41, 541 See also,
    • (c) Spohn, M.; Strahle, J.; Hiller, W. Z. Naturforsch. B. 1986, 41, 541 See also,
  • 43
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    • 20b
    • 20b
  • 49
    • 0021756737 scopus 로고    scopus 로고
    • We estimate a pKa, value of ∼20 for ketone 8a on the basis of the aqueous pKaaq of 19 reported for acetone, see:Guthrie, J. P, Cossar, J, Klym, A. J. Am. Chem. Soc. 1984, 106, 1351
    • aq of 19 reported for acetone, see:Guthrie, J. P.; Cossar, J.; Klym, A. J. Am. Chem. Soc. 1984, 106, 1351.
  • 51
    • 0001328629 scopus 로고    scopus 로고
    • 26b (a) Levi, A.; Modena, G.; Scorrano, G. J. Am. Chem. Soc. 1974, 96, 6585.
    • 26b (a) Levi, A.; Modena, G.; Scorrano, G. J. Am. Chem. Soc. 1974, 96, 6585.
  • 59
    • 3543021019 scopus 로고
    • As reported for 2-ethoxycarbonylcyclopentanone
    • As reported for 2-ethoxycarbonylcyclopentanone: Pearson, R. G.; Dillon, R. L. J. Am. Chem. Soc. 1953, 75, 2439.
    • (1953) J. Am. Chem. Soc , vol.75 , pp. 2439
    • Pearson, R.G.1    Dillon, R.L.2
  • 62
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    • 31P NMR spectrum of the reaction solution indicates that both 2a and 3a decompose at temperatures above 0°C to unidentified products, probably by replacement of the β-keto ester ligand by the sulfonate anion.
    • 31P NMR spectrum of the reaction solution indicates that both 2a and 3a decompose at temperatures above 0°C to unidentified products, probably by replacement of the β-keto ester ligand by the sulfonate anion.
  • 63
    • 50449205255 scopus 로고    scopus 로고
    • At concentrations above 0.04 M in CD2Cl2. The product ratio is calculated by integration of the 31P NMR spectrum of the reaction solution. When (Et3O)PF6 is used to synthesize 2a from 1, no detectable amount of 3a is observed by NMR spectroscopy, probably because Et3O+ reacts with traces of water to give Et2OH
    • +.
  • 71
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    • In the Ru/PNNP-catalyzed fluorination of β-keto esters, we have observed that the fluorinated β-keto ester remains coordinated to ruthenium, although it binds more weakly to ruthenium than the substrate 4a.14
    • 14


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.