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Volumn , Issue , 2007, Pages 77-94

Enamine Catalysis: Direct Conjugate Additions via Enamine Activation

Author keywords

Addition of aldehydes to nitroolefins and alkylidene malonates; Addition of ketones to nitroolefins and alkylidene malonates; Direct conjugate additions via enamine activation; Factors determining the stereoselectivity of the organocatalytic conjugate additions

Indexed keywords


EID: 84891037969     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527610945.ch2c     Document Type: Chapter
Times cited : (3)

References (71)
  • 2
    • 84891004017 scopus 로고    scopus 로고
    • in: E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Springer-Verlag, Berlin, Germany, Chapter 31.2.
    • M. Yamaguchi, in: E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis I-III. Springer-Verlag, Berlin, Germany, 1999, Chapter 31.2.
    • (1999) Comprehensive Asymmetric Catalysis I-III
    • Yamaguchi, M.1
  • 3
    • 0034612973 scopus 로고    scopus 로고
    • For reviews, see:
    • For reviews, see: M.P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061;
    • (2000) Tetrahedron , vol.56 , pp. 8033-8061
    • Sibi, M.P.1    Manyem, S.2
  • 20
    • 0012411122 scopus 로고    scopus 로고
    • B. List, Tetrahedron 2002, 58, 5572-5590;
    • (2002) Tetrahedron , vol.58 , pp. 5572-5590
    • List, B.1
  • 22
    • 0034750244 scopus 로고    scopus 로고
    • B. List, Synlett 2001, 1675-1686.
    • (2001) Synlett , pp. 1675-1686
    • List, B.1
  • 23
    • 84891000412 scopus 로고    scopus 로고
    • As defined by List in Ref. [4n]: "There are two aminocatalytic pathways. Iminium catalysis directly utilizes the higher reactivity of the iminium ion in comparison to the carbonyl species and facilitates Knoevenagel-type condensations, cyclo-and nucleophilic additions, and cleavage of s-bonds adjacent to the α-carbon. Enamine catalysis on the other hand involves catalytically generated enamine intermediates that are formed via deprotonation of an iminium ion, and react with various electrophiles or undergo pericyclic reactions."
    • As defined by List in Ref. [4n]: "There are two aminocatalytic pathways. Iminium catalysis directly utilizes the higher reactivity of the iminium ion in comparison to the carbonyl species and facilitates Knoevenagel-type condensations, cyclo-and nucleophilic additions, and cleavage of s-bonds adjacent to the α-carbon. Enamine catalysis on the other hand involves catalytically generated enamine intermediates that are formed via deprotonation of an iminium ion, and react with various electrophiles or undergo pericyclic reactions."
  • 43
    • 84891003324 scopus 로고    scopus 로고
    • Decreasing the reaction temperature results in an increase of the overall selectivity and a dramatic decrease in the conversion.
    • Decreasing the reaction temperature results in an increase of the overall selectivity and a dramatic decrease in the conversion.
  • 51
    • 84890971925 scopus 로고    scopus 로고
    • For related chiral (thio)urea catalyst-mediated electrophilic activation of enones in conjugate addition, see also Chapter 6.
    • For related chiral (thio)urea catalyst-mediated electrophilic activation of enones in conjugate addition, see also Chapter 6.
  • 62
    • 33747594792 scopus 로고    scopus 로고
    • For related fluorous derivatives as catalysts in Michael-type additions, see:
    • For related fluorous derivatives as catalysts in Michael-type additions, see: W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354-10355.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 10354-10355
    • Wang, W.1    Li, H.2    Wang, J.3    Zu, L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.