메뉴 건너뛰기




Volumn 70, Issue 18, 2005, Pages 7451-7454

Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to (2-pyridyl)sulfonyl imines of chalcones

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; COPPER;

EID: 24144479262     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0511602     Document Type: Article
Times cited : (75)

References (55)
  • 1
    • 11844293650 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, Supplement to Chapter 31.1
    • For recent reviews on enantioselective conjugate addition, see: (a) Tomioka, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 2004; Supplement to Chapter 31.1, p 109.
    • (2004) Comprehensive Asymmetric Catalysis , pp. 109
    • Tomioka, K.1
  • 8
    • 33645593287 scopus 로고    scopus 로고
    • Otera, J., Ed.; Wiley-VCH: Weinheim, Chapter 12
    • Tomioka, K. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 12. For the Zn-Cu transmetalation and the reaction pathway of the Cu-catalyzed 1,4-addition of organozinc reagenst, see ref 1c.
    • (2000) Modern Carbonyl Chemistry
    • Tomioka, K.1
  • 14
    • 0347753811 scopus 로고    scopus 로고
    • For enantioselective catalytic 1,2-additions to ketimines, see: (a) Jiang, B., Si, Y. Angew. Chem., Int. Ed. 2004, 43, 216.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 216
    • Jiang, B.1    Si, Y.2
  • 21
    • 0034595320 scopus 로고    scopus 로고
    • For the concept of controlling stereoselectivity with the aid of a removable reagent-directing group, see: (a) Breit, B. Chem. Eur. J. 2000, 6, 1519.
    • (2000) Chem. Eur. J. , vol.6 , pp. 1519
    • Breit, B.1
  • 28
    • 37049109955 scopus 로고
    • and references therein
    • The (E) stereochemistry of the C=C double bond was established on the basis of the observed coupling constant between the two olefinic protons (J ≈ 16 Hz in all cases). On the other hand, it is known that the barrier to E/Z interconversion at the C=N bond is very low for N-sulfonylimines (see, for instance: Brown, C.; Hudson, R. F.; Record, K. A. F. J. Chem. Soc., Perkin Trans. 2 1978, 822 and references therein).
    • (1978) J. Chem. Soc., Perkin Trans. 2 , pp. 822
    • Brown, C.1    Hudson, R.F.2    Record, K.A.F.3
  • 29
    • 33645591094 scopus 로고    scopus 로고
    • note
    • The (Z) stereochemistry of N-sulfonylenamines was assigned by NMR on compound 14. The observation of a strong NOE signal between the olefinic hydrogen and the ortho-protons on the phenyl group, coupled with the absence of NOE of the latter with the methyl group, was of particular diagnostic value.
  • 33
    • 0034624432 scopus 로고    scopus 로고
    • 2Zn to the 2-pyridylsulfonylimine of cinnamaldehyde occurred with complete 1,2-selectivity instead of 1,4-selectivity. For 1,2-addition processes to α,β-unsaturated aldimines, see: Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 976
    • Hayashi, T.1    Ishigedani, M.2
  • 35
    • 33645585309 scopus 로고    scopus 로고
    • note
    • The same lack of reactivity for substrate 1a was also observed in the presence of the chiral ligand IV.
  • 36
    • 0004246896 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim, Germany
    • For recent reviews on copper-catalyzed reactions, see: (a) Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
    • (2002) Modern Organocopper Chemistry
    • Krause, N.1
  • 39
    • 0033935279 scopus 로고    scopus 로고
    • For a review on phosphoramidite ligands in asymmetric catalysis, see: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 346
    • Feringa, B.L.1
  • 53
    • 33645586797 scopus 로고    scopus 로고
    • note
    • 2 and DCE, the reaction occurs with similar yield but lower enantioselectivity.
  • 55
    • 33645584171 scopus 로고    scopus 로고
    • note
    • For general remarks, see ref 15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.