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Volumn , Issue 12, 2004, Pages 2139-2142

Copper-catalyzed conjugate addition of a bis(triorganosilyl) zinc and a methyl(triorganosilyl) magnesium

Author keywords

Catalysis; Copper; Cuprates; Silicon; Zinc

Indexed keywords

CARBONYL DERIVATIVE; COPPER; LIGAND; MAGNESIUM DERIVATIVE; REAGENT; SILANE DERIVATIVE; ZINC DERIVATIVE;

EID: 5644244497     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831331     Document Type: Article
Times cited : (55)

References (42)
  • 1
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    • For comprehensive reviews on the Tamao-Fleming oxidation see: (a) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
    • (1996) Tetrahedron , vol.52 , pp. 7599
    • Jones, G.R.1    Landais, Y.2
  • 7
    • 5644227519 scopus 로고    scopus 로고
    • Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart
    • (c) Singer, R. D. In Science of Synthesis, Vol. 4; Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart, 2002, 231.
    • (2002) Science of Synthesis , vol.4 , pp. 231
    • Singer, R.D.1
  • 26
    • 34248152109 scopus 로고    scopus 로고
    • Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart
    • Hameon, I.; Singer, R. D. In Science of Synthesis, Vol. 4; Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart, 2002, 225.
    • (2002) Science of Synthesis , vol.4 , pp. 225
    • Hameon, I.1    Singer, R.D.2
  • 27
    • 0008757976 scopus 로고
    • For a single report on the preparation of 3 and an application in a silyl metalation reaction see: Morizawa, Y.; Oda, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 1163; this seminal publication also includes the magnesium reagent 7.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1163
    • Morizawa, Y.1    Oda, H.2    Oshima, K.3    Nozaki, H.4
  • 28
    • 5644233879 scopus 로고    scopus 로고
    • note
    • 2O) was added accompanied by a color change from red to yellowish brown. The reaction mixture was maintained at this temperature for further 15 min and was ready to use.
  • 29
    • 5644227520 scopus 로고    scopus 로고
    • note
    • 4), the solvents were evaporated under reduced pressure and the resulting crude product 5 was purified by flash chromatography on silica gel using cyclohexane-MTBE solvent mixtures,
  • 30
    • 5644302350 scopus 로고    scopus 로고
    • note
    • 4Cl (25 mL). Work-up and purification of 5 as described for Method A.
  • 31
    • 5644249421 scopus 로고    scopus 로고
    • note
    • 2.
  • 32
    • 5644267904 scopus 로고    scopus 로고
    • note
    • 3SiZnCl under copper catalysis.
  • 33
    • 33746803229 scopus 로고
    • 3SiLi undergoes rapid 1,4-additon to β-monosubstituted ketones in the absence of any copper catalyst. See: Still, W. C. J. Org. Chem. 1976, 41, 3063.
    • (1976) J. Org. Chem. , vol.41 , pp. 3063
    • Still, W.C.1
  • 34
    • 5644272804 scopus 로고    scopus 로고
    • note
    • 2SiLi (2).
  • 35
    • 0141581512 scopus 로고    scopus 로고
    • Krause, N., Ed.; Wiley-VCH: Weinheim
    • 2 is believed to be reduced in situ as described for the conjugate addition of dialkylzincs: Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modem Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, 224.
    • (2002) Modem Organocopper Chemistry , pp. 224
    • Feringa, B.L.1    Naasz, R.2    Imbos, R.3    Arnold, L.A.4
  • 40
    • 5644271618 scopus 로고    scopus 로고
    • note
    • The generation of 3 from 1 produces a fourfold excess of LiCl, which might function as a Lewis acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.