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Volumn 9, Issue 2, 2011, Pages 363-366

Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ONE-POT SYNTHESIS; ORGANOCATALYTIC; THREE COMPONENT REACTIONS; UNSATURATED KETONES; VINYL KETONES;

EID: 78650754320     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00644k     Document Type: Article
Times cited : (10)

References (29)
  • 10
    • 31544434530 scopus 로고    scopus 로고
    • For an overview, see
    • A. Dömling Chem. Rev. 2006 106 17
    • (2006) Chem. Rev. , vol.106 , pp. 17
    • Dömling, A.1
  • 17
    • 37649016631 scopus 로고    scopus 로고
    • Organocatalytic Enantioselective Morita-Baylis-Hillman Reactions
    • ed. P. I. Dalko, Wiley-VCH, Weinheim, Germany,; recent reviews for application of Baylis-Hillman adduct, see
    • C. Menozzi and P. I. Dalko, Organocatalytic Enantioselective Morita-Baylis-Hillman Reactions. In Enantioselective Organocatalysis, Reactions and Experimental Procedures, ed., P. I. Dalko,, Wiley-VCH, Weinheim, Germany, 2007
    • (2007) Enantioselective Organocatalysis, Reactions and Experimental Procedures
    • Menozzi, C.1    Dalko, P.I.2
  • 20
    • 77956464073 scopus 로고    scopus 로고
    • For selected literature about the addition of carbon nucleophile to Baylis-Hillman adduct, see
    • D. Basavaiah B. S. Reddy S. S. Badsara Chem. Rev. 2010 110 5447
    • (2010) Chem. Rev. , vol.110 , pp. 5447
    • Basavaiah, D.1    Reddy, B.S.2    Badsara, S.S.3
  • 28
    • 33744469835 scopus 로고    scopus 로고
    • The dimerization of methyl vinyl ketone (2a) occurred during the reaction progress, and therefore it is necessary to use increasing amount of 2a when the reaction time of the whole reaction progress was getting longer. In case of preparation of 4i, there was no further improvement when increasing amount of 2a was used The Baylis-Hillman adduct resulting from 1a and 2a was furnished efficiently (5 h, 100% conversion). However, the further addition of 3a toward the Baylis-Hillman adduct in the presence of DABCO proceeded very slowly (7 days, 86% conversion), leading to the expected adduct 4a in 84% yield For recent application of functionalized α,β-unsaturated ketones as inhibitors of specific classes of cysteine proteases, see
    • M. Shi Y.-H. Liu Org. Biomol. Chem. 2006 4 1468
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 1468
    • Shi, M.1    Liu, Y.-H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.