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Volumn 351, Issue 11-12, 2009, Pages 1946-1954

Ferric chloride hexahydrate-catalyzed highly regio- And stereoselective conjugate addition reaction of 2,3-allenoates with grignard reagents: An efficient synthesis of β,γ-alkenoates

Author keywords

Allenes; Esters; Grignard reagents; Iron; Michael addition

Indexed keywords


EID: 68949098577     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900091     Document Type: Article
Times cited : (33)

References (64)
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    • For some recent reports on the synthesis of β,γ-unsaturated alkenoates, see, a
    • For some recent reports on the synthesis of β,γ-unsaturated alkenoates, see : a) F. Brebion, J.-P. Goddard, L. Fensterbank, M. Malacria, Org. Lett. 2008, 10, 1917;
    • (2008) Org. Lett , vol.10 , pp. 1917
    • Brebion, F.1    Goddard, J.-P.2    Fensterbank, L.3    Malacria, M.4
  • 9
    • 68949102662 scopus 로고    scopus 로고
    • Modern Allene Chemistry, (Eds. : N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004;
    • a) Modern Allene Chemistry, (Eds. : N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004;
  • 10
    • 22944485617 scopus 로고    scopus 로고
    • b) S. Ma, Chem. Rev. 2005, 105, 2829.
    • (2005) Chem. Rev , vol.105 , pp. 2829
    • Ma, S.1
  • 17
    • 84890999876 scopus 로고    scopus 로고
    • For a general overview on iron catalysis in organic chemistry, see: a, Ed, B. Plietker, Wiley-VCH, Weinheim
    • For a general overview on iron catalysis in organic chemistry, see: a) Iron Catalysis in Organic Chemistry, (Ed.: B. Plietker), Wiley-VCH, Weinheim, 2008;
    • (2008) Iron Catalysis in Organic Chemistry
  • 24
    • 51049092766 scopus 로고    scopus 로고
    • 3-catalyzed reactions, see: a N. Xia, M. Taillefer, Chem. Eur. J. 2008, 14, 6037;
    • 3-catalyzed reactions, see: a) N. Xia, M. Taillefer, Chem. Eur. J. 2008, 14, 6037;
  • 40
    • 68949112741 scopus 로고    scopus 로고
    • 2O as catalyst, see: a K. Komeyama, T. Morimoto, K. Takaki, Angew. Chem. 2006, 118, 3004;
    • 2O as catalyst, see: a) K. Komeyama, T. Morimoto, K. Takaki, Angew. Chem. 2006, 118, 3004;
  • 50
    • 68949123982 scopus 로고    scopus 로고
    • Due to the high electron density at C(2) of a metallodienolate, reaction at the a-position affording β,γ-unsaturated carbonyl compounds is favored kinetically over reaction at the y-position affording α,β-unsaturated carbonyl compounds, see: a) I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley-Interscience, New York, 1996, p 45;
    • Due to the high electron density at C(2) of a metallodienolate, reaction at the a-position affording β,γ-unsaturated carbonyl compounds is favored kinetically over reaction at the y-position affording α,β-unsaturated carbonyl compounds, see: a) I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley-Interscience, New York, 1996, p 45;
  • 51
    • 0002061964 scopus 로고    scopus 로고
    • J. L. Herrmann, G. R. Kieczy-kowski, R. H. Schlessinger, Tetrahedron Lett. 1973, 14, 2433. For some recent typical examples of reactions of dienolates at the a-position, see:
    • b) J. L. Herrmann, G. R. Kieczy-kowski, R. H. Schlessinger, Tetrahedron Lett. 1973, 14, 2433. For some recent typical examples of reactions of dienolates at the a-position, see:
  • 64
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    • + is 0.96 Å.
    • + is 0.96 Å.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.