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Volumn 126, Issue 18, 2004, Pages 5672-5673

Organocatalytic Enantioselective Conjugate Addition to Alkynones

Author keywords

[No Author keywords available]

Indexed keywords

(2 PYRROLIDINYLMETHYL)PYRROLIDINE; ACETYLCYCLOPENTANONE; ALKANONE; ALKYNE; ORGANIC COMPOUND; PYRROLIDINE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

EID: 2442629288     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0493594     Document Type: Article
Times cited : (148)

References (36)
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    • Most recent examples of sterocontrolled quanternary centers formation via conjugate addition: (k) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11240
    • Hamashima, Y.1    Hotta, D.2    Sodeoka, M.3
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    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1688
  • 17
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    • For stoichiometric sparteine-mediated addition to alkynones see: Papillon, J. P. N.; Taylor, R. J. K. Org. Lett. 2002, 4, 119; diastereoselective addition: Guillena, G.; Najera, C. J. Org. Chem. 2000, 65, 7310.
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    • Papillon, J.P.N.1    Taylor, R.J.K.2
  • 18
    • 0034602345 scopus 로고    scopus 로고
    • For stoichiometric sparteine-mediated addition to alkynones see: Papillon, J. P. N.; Taylor, R. J. K. Org. Lett. 2002, 4, 119; diastereoselective addition: Guillena, G.; Najera, C. J. Org. Chem. 2000, 65, 7310.
    • (2000) J. Org. Chem. , vol.65 , pp. 7310
    • Guillena, G.1    Najera, C.2
  • 19
    • 0037458985 scopus 로고    scopus 로고
    • For racemic conjugate Michael additions of carbon nucleophiles to alkynones see, e.g.: (a) Hattori, K.; Grossman, R. B. J. Org. Chem. 2003, 68, 1409.
    • (2003) J. Org. Chem. , vol.68 , pp. 1409
    • Hattori, K.1    Grossman, R.B.2
  • 28
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    • note
    • Cinchona alkaloids bearing an unprotected hydroxyl functionality gave in the reaction conditions O-addition to alkynones. In entries 2 and 3, the active catalysts area 2:1 E/Z mixture of 4-(O-cinchonin)-buten-2-one and 4-(O-quinin)-buten-2-one, respectively. Alkynones are known to react smoothly with hydroxy functionalities.
  • 29
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    • Tae et al. recently reported a stoichiometric racemic addition of β-diketones to ethyl propyolate in 45% yield: Tae, J.; Kim, K.-O. Tetrahedron Lett. 2003, 44, 2125. For Michael conjugate addition of cyclic β-diketones see, e.g.: (a) Challenger, S.; Derrick, A.; Silk, T. V. Synth. Commun. 2002, 2911.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2125
    • Tae, J.1    Kim, K.-O.2
  • 30
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    • Tae et al. recently reported a stoichiometric racemic addition of β-diketones to ethyl propyolate in 45% yield: Tae, J.; Kim, K.-O. Tetrahedron Lett. 2003, 44, 2125. For Michael conjugate addition of cyclic β-diketones see, e.g.: (a) Challenger, S.; Derrick, A.; Silk, T. V. Synth. Commun. 2002, 2911.
    • (2002) Synth. Commun. , pp. 2911
    • Challenger, S.1    Derrick, A.2    Silk, T.V.3
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  • 35
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    • and ref 1k
    • (e) There are very limited examples in the literature of asymmetric Michael additions of β-diketones: see e.g.: Chen, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Org. Chem. 2003, 68, 871 and ref 1k.
    • (2003) J. Org. Chem. , vol.68 , pp. 871
    • Chen, Z.1    Zhu, G.2    Jiang, Q.3    Xiao, D.4    Cao, P.5    Zhang, X.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.