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Volumn 13, Issue 45, 2015, Pages 11039-11045

Organocatalytic asymmetric desymmetrization of 4,4-disubstituted cyclohexadienones via an intermolecular Diels-Alder reaction

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Indexed keywords

CHEMICAL REACTIONS;

EID: 84947422284     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c5ob01760b     Document Type: Article
Times cited : (23)

References (46)
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    • 85006224747 scopus 로고    scopus 로고
    • in, ed. I. Dalko, Wiley-VCH, Weinheim, ch. 11, In order to expand the scope of diene, we examined the phosphoric acid catalyzed Diels-Alder reaction of dienone 1a with Danishefsky's diene, but the Diels-Alder reaction did not proceed
    • K. Mori and T. Akiyama, in Comprehensive Enantioselective Organocatalysis, ed., P. I. Dalko, Wiley-VCH, Weinheim, 2013, vol. 2, ch. 11, pp. 289-314
    • (2013) Comprehensive Enantioselective Organocatalysis , vol.2 , pp. 289-314
    • Mori, K.1    Akiyama, T.2
  • 40
    • 0032748432 scopus 로고    scopus 로고
    • In our previous study (ref. 8a), we examined the retro-Diels-Alder reaction of cycloadduct derivatives, generated from cyclohexadienone bearing a spiro-lactone-ring at the C4 position. The C-O bond in the spiro-lactone-ring is weaker than the C4 substituent of compounds 3a and 4, but the epimerization at the C4 position was not observed. So, we believe that the reaction conditions did not induce the epimerization at the C4 position For reviews
    • S. A. Kozmin V. H. Rawal J. Am. Chem. Soc. 1999 121 9562 9573
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9562-9573
    • Kozmin, S.A.1    Rawal, V.H.2
  • 44
    • 39549121796 scopus 로고    scopus 로고
    • 2P(O)OH-catalyzed Diels-Alder reaction also indicated the unexpected interaction between the Lewis-basic site of the phosphoric acid moiety and the C-H bond of cyclopentadiene (see the ESI)
    • M. Y. Lee K. H. Kim S. Jiang Y. H. Jung J. Y. Sim G.-S. Hwang D. H. Ryu Tetrahedron Lett. 2008 49 1965 1967
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1965-1967
    • Lee, M.Y.1    Kim, K.H.2    Jiang, S.3    Jung, Y.H.4    Sim, J.Y.5    Hwang, G.-S.6    Ryu, D.H.7
  • 46
    • 70450206724 scopus 로고    scopus 로고
    • Gaussian Inc., Wallingford, CT, (full reference in ESI)
    • M. J. Frisch, et al., Gaussian 09, Gaussian Inc., Wallingford, CT, 2009
    • (2009) Gaussian 09
    • Frisch, M.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.