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Volumn 133, Issue 11, 2011, Pages 3740-3743

A straightforward synthesis of cyclobutenones via a tandem Michael addition/cyclization reaction of 2,3-allenoates with organozincs

Author keywords

[No Author keywords available]

Indexed keywords

EFFICIENT METHOD; ORGANOZINC REAGENTS; RING STRAINS;

EID: 79952775227     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1108694     Document Type: Article
Times cited : (35)

References (59)
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    • There are few reports on the intramolecular 1,2-addition/elimination cyclization to form 4-membered cyclic products
    • There are few reports on the intramolecular 1,2-addition/elimination cyclization to form 4-membered cyclic products: McGarvey, G. J.; Kimura, M. J. Org. Chem. 1985, 50, 4655
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    • McGarvey, G.J.1    Kimura, M.2
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    • 8-catalyzed transformation of ethyl 2,4,4-triphenyl-2,3-butadienoate to 3-ethoxy-2,4,4-triphenylcyclobutenone in 12% yield with 20% of conversion, see
    • 8-catalyzed transformation of ethyl 2,4,4-triphenyl-2,3-butadienoate to 3-ethoxy-2,4,4-triphenylcyclobutenone in 12% yield with 20% of conversion, see: Trifonov, L. S.; Orahovats, A. S.; Heimgartner, H. Helv. Chim. Acta 1987, 70, 1070
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    • note
    • int = 0.0222), number of observations [>2σ(I)] 2163, parameters: 172. CCDC 800810.
  • 38
    • 36749007137 scopus 로고    scopus 로고
    • For our studies on the reaction of 2,3-allenoates with Grignard reagents affording conjugate addition products, see
    • For our studies on the reaction of 2,3-allenoates with Grignard reagents affording conjugate addition products, see: Lu, Z.; Chai, G.; Ma, S. J. Am. Chem. Soc. 2007, 129, 14546
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 14546
    • Lu, Z.1    Chai, G.2    Ma, S.3
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    • The β,γ-unsaturated enones are important and versatile intermediates in organic synthesis and exist widely as functional groups in many natural products, see
    • The β,γ-unsaturated enones are important and versatile intermediates in organic synthesis and exist widely as functional groups in many natural products, see: Thomas, A. F.; Thommen, W.; Willhalm, B.; Hagaman, E. W.; Wenkert, E. Helv. Chim. Acta 1974, 57, 2055
    • (1974) Helv. Chim. Acta , vol.57 , pp. 2055
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    • Due to the possible migration of the β,γ-C=C bond to the conjugated α,β-position, they are difficult to prepare. For some representatives on the synthesis of β,γ-unsaturated enones, see
    • Due to the possible migration of the β,γ-C=C bond to the conjugated α,β-position, they are difficult to prepare. For some representatives on the synthesis of β,γ-unsaturated enones, see: Cazes, B.; Julia, S. Tetrahedron Lett. 1974, 15, 2077
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    • There are two reports on the electrocyclic ring opening of cyclobutenone derivatives with lithium reagents, see cyclobutenone ethylenedithioacetals:;, Phenyl- and vinylcyclobutanones:; Chem. Commun. 2010, 8845
    • There are two reports on the electrocyclic ring opening of cyclobutenone derivatives with lithium reagents, see cyclobutenone ethylenedithioacetals: Regenhardt, W.; Schaumann, E.; Moore, H. W. Synthesis 2001, 1076 Phenyl- and vinylcyclobutanones: Ji, X.; Wang, Q.; Goeke, A. Chem. Commun. 2010, 8845
    • (2001) Synthesis , pp. 1076
    • Regenhardt, W.1    Schaumann, E.2    Moore, H.W.3    Ji, X.4    Wang, Q.5    Goeke, A.6
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    • note
    • int = 0.0541), number of observations [>2σ(I)] 6270, parameters: 660. CCDC 800811.
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    • Ma, S. Chem. Rev. 2005, 105, 2829
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.