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Volumn 3, Issue 7, 2001, Pages 983-985

Highly diastereoselective Michael addition of α-hydroxy acid derivatives and enantioselective synthesis of (+)-crobarbatic acid

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ARTICLE;

EID: 0042233658     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.5555/ol0069507     Document Type: Article
Times cited : (28)

References (37)
  • 1
    • 0011928573 scopus 로고
    • In noncatalytic additions to α,β-unsaturated carbonyl compounds
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 7
    • (a) Tomioka, K.; Koga, K. In Noncatalytic Additions to α,β-Unsaturated Carbonyl Compounds. In Asymmetric Synthesis, Vol. 2; Morrison, J. D., Ed.; Academic Press: New York, 1983; Chapter 7.
    • (1983) Asymmetric Synthesis , vol.2
    • Tomioka, K.1    Koga, K.2
  • 2
    • 84918169275 scopus 로고
    • Organometallic addition reactions to enatiomerically pure vinylic sulfoxides
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 8
    • (b) Posner, G. H. Organometallic Addition Reactions to Enatiomerically Pure Vinylic Sulfoxides. In Asymmetric Synthesis, Vol. 2; Morrison, J. D., Ed.; Academic Press: New York, 1983; Chapter 8.
    • (1983) Asymmetric Synthesis , vol.2
    • Posner, G.H.1
  • 17
    • 0003905731 scopus 로고
    • Morrison, J. D., Scott, J. W., Eds.; Academic Press: New York
    • (a) Scott, J. W. In Asymmetric Synthesis; Morrison, J. D., Scott, J. W., Eds.; Academic Press: New York, 1984; Vol. 4.
    • (1984) Asymmetric Synthesis , vol.4
    • Scott, J.W.1
  • 18
    • 0003598094 scopus 로고
    • Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt
    • (b) Seeback, D. In Modern Synthetic Methods; Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt, 1980.
    • (1980) Modern Synthetic Methods
    • Seeback, D.1
  • 24
    • 0001321780 scopus 로고
    • It has been found that the E lithium enolate of ethyl propionate reacted with ethyl (E)-crotonate gave anti and syn 1,4-adducts in a ratio of 71:29. The stereoselectivity was increased to 10:1 if HMPA was added after enolate formation and further increased to >20:1 if HMPA was added prior to enolate formation. See: Yamaguchi, M.; Tsukamoto, M.; Tanaka, S.; Hirao, I. Tetrahedron Lett. 1984, 25, 5661.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5661
    • Yamaguchi, M.1    Tsukamoto, M.2    Tanaka, S.3    Hirao, I.4
  • 28
    • 0041789463 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-149424 for 3, CCDC-149423 for 5g, and CCDC-149425 for (+)-8. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax (+44) 1223-336-033; e-mail deposit@ ccdc.cam.ac.uk).
  • 29
    • 0041288909 scopus 로고    scopus 로고
    • note
    • Further evidence for other Michael adducts without X-ray crystallographic analysis were confirmed by NOE experiments of the corresponding products after hydrolysis and lactonization [eqs 3 and 4]. For details, see Supporting Information.
  • 35
    • 0041288910 scopus 로고    scopus 로고
    • note
    • 2O).


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