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Volumn , Issue , 2010, Pages 219-293

Iminium Activation in Catalytic Enantioselective Conjugate Additions

Author keywords

Asymmetric catalysis; Cascade reaction; Conjugate addition; Michael reaction; Organic reactions; Organocatalysis; Stereoselective synthesis

Indexed keywords


EID: 84887201116     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630578.ch6     Document Type: Chapter
Times cited : (7)

References (240)
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    • For some general reviews covering amine-catalyzed enantioselective reactions see
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    • For some more general reviews on asymmetric organocatalysis see
    • Mukherjee, S. and List, B. (2007) Nature, 129, 7498; For some more general reviews on asymmetric organocatalysis see:
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    • Special Issue on Organocatalysis
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    • For some reviews on organocatalytic conjugate additions see
    • For some reviews on organocatalytic conjugate additions see: (a) Vicario, J.L., Badia, D., and Carrillo, L. (2007) Synthesis, 2065;
    • (2007) Synthesis , pp. 2065
    • Vicario, J.L.1    Badia, D.2    Carrillo, L.3
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    • For a specific review covering organocatalytic reactions via iminium activation, see also Ref. [2b]
    • Sulzer-Mosse, S. and Alexakis, A. (2007) Chem. Commun., 3123. For a specific review covering organocatalytic reactions via iminium activation, see also Ref. [2b].
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    • In 1993 Belokon reported the l-prolinol-catalyzed addition of methyl nitroacetate to crotonaldehyde proceeding with low enantioselectivity, In 2000, Barbas carried out the Robinson annulation between 2-methyl-1,3-cyclohexanedione and methyl vinyl ketone catalyzed by several chiral amines, and reported that the process stopped in many cases after the conjugate addition step. However, neither yields nor enantioselectivities were given for this case
    • In 1993, Belokon reported the l-prolinol-catalyzed addition of methyl nitroacetate to crotonaldehyde proceeding with low enantioselectivity: (a) Belokon, Y.N., Kochetkov, K.A., Churkina, T.D., Ikonnikov, N.S., Orlova, S.A., Kuzmina, N.A., and Bodrov, D.E. (1993) Russ. Chem. Bull., 9, 1591; In 2000, Barbas carried out the Robinson annulation between 2-methyl-1,3-cyclohexanedione and methyl vinyl ketone catalyzed by several chiral amines, and reported that the process stopped in many cases after the conjugate addition step. However, neither yields nor enantioselectivities were given for this case.
    • (1993) Russ. Chem. Bull. , vol.9 , pp. 1591
    • Belokon, Y.N.1    Kochetkov, K.A.2    Churkina, T.D.3    Ikonnikov, N.S.4    Orlova, S.A.5    Kuzmina, N.A.6    Bodrov, D.E.7
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    • For some reviews see
    • For some reviews see (a) Lattanzi, A. (2009) Chem. Commun., 1452;
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    • For an extension of this methodology to the one-pot asymmetric synthesis of substituted 1,4-dihydropyridines see
    • Brandau, S., Landa, A., Franzen, J., Marigo, M., and Jørgensen, K.A. (2006) Angew. Chem., Int. Ed., 45, 4305; For an extension of this methodology to the one-pot asymmetric synthesis of substituted 1,4-dihydropyridines see
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 4305
    • Brandau, S.1    Landa, A.2    Franzen, J.3    Marigo, M.4    Jørgensen, K.A.5
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    • For a related intramolecular reaction see
    • Lee, S. and MacMillan, D.W.C. (2007) J. Am. Chem. Soc., 129, 15438; For a related intramolecular reaction see
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    • Lee, S.1    MacMillan, D.W.C.2
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  • 129
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    • For a related example using a chiral sulfonyl hydrazine as organocatalyst see
    • Vesely, J., Ibrahem, I., Rios, R., Zhao, G.-L., Xu, Y., and Córdova, A. (2007) Tetrahedron Lett., 48, 2193; For a related example using a chiral sulfonyl hydrazine as organocatalyst see
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2193
    • Vesely, J.1    Ibrahem, I.2    Rios, R.3    Zhao, G.-L.4    Xu, Y.5    Córdova, A.6
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    • For some selected reviews see
    • For some selected reviews see (a) Ismabery, N. and Lavila, R. (2008) Chem. Eur. J., 14, 8444;
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    • Ismabery, N.1    Lavila, R.2
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    • This concept was also applied to the use of enals as substrates
    • Wang, X., Reisinger, C.M., and List, B. (2008) J. Am. Chem. Soc., 130, 6070; This concept was also applied to the use of enals as substrates:
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 6070
    • Wang, X.1    Reisinger, C.M.2    List, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.