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Volumn , Issue 5, 2007, Pages 809-811

Gallium(III) chloride catalyzed stereoselective synthesis of E-configured α,β-unsaturated ketones

Author keywords

, unsaturated ketones; Activated alkynes; Gallium(III) chloride; Ynones

Indexed keywords

GALLIUM CHLORIDE; KETONE DERIVATIVE;

EID: 33947714901     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970760     Document Type: Article
Times cited : (16)

References (33)
  • 1
    • 33947722090 scopus 로고    scopus 로고
    • IICT Communication No. 061125.
    • IICT Communication No. 061125.
  • 2
  • 3
    • 33947724369 scopus 로고    scopus 로고
    • For a review on the synthetic applications of α,β-unsaturated ketones, see: (a) The Chemistry of Enones; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1989, 281.
    • For a review on the synthetic applications of α,β-unsaturated ketones, see: (a) The Chemistry of Enones; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1989, 281.
  • 5
    • 84906288824 scopus 로고    scopus 로고
    • For a recent review of the syntheses of α,β-unsaturated ketones, see:, Katritzky, A. R, Taylor, R. J. K, Eds, Elsevier Ltd: Oxford, UK
    • For a recent review of the syntheses of α,β-unsaturated ketones, see: Foster, C. E.; Mackie, P. R. In Comprehensive Organic Functional Group Transformations II, Vol. 3; Katritzky, A. R.; Taylor, R. J. K., Eds.; Elsevier Ltd: Oxford, UK, 2005, 215.
    • (2005) Comprehensive Organic Functional Group Transformations II , vol.3 , pp. 215
    • Foster, C.E.1    Mackie, P.R.2
  • 19
    • 33645773178 scopus 로고    scopus 로고
    • Cossy, J, Ed, Thieme: Stuttgart
    • (a) Figadere, B.; Franck, X. In Science of Synthesis, Vol. 26; Cossy, J., Ed.; Thieme: Stuttgart, 2004, 401.
    • (2004) Science of Synthesis , vol.26 , pp. 401
    • Figadere, B.1    Franck, X.2
  • 33
    • 33947714788 scopus 로고    scopus 로고
    • General Procedure. To the reaction mixture containing substrate 1 (1.0 mmol, CH2Cl2 (10 mL) and alkynone 2 (1.5 mmol) was added a catalytic amount of GaCl3 (0.1 mmol, The resulting mixture was stirred at r.t. for the appropriate time (Table 1, After completion of the reaction as indicated by TLC, EtOAc (20 mL) and H2O (10 mL) were added to the reaction mixture and further stirred at r.t. for additional 10 min. Then, the EtOAc layer was separated and aqueous phase was extracted again with EtOAc (2 x 10 mL, The combined extracts were washed with brine, dried over anhyd Na2SO4 and concentrated in vacuo. The resulting crude product was purified by column chromatography on silica gel (Merck, 60-120 mesh, EtOAc-hexane, 2:8) to afford a pure product. Spectral Data for Selected Products: Compound 3a: IR KBr, νmax, 2924, 2856, 1732, 1556, 1458, 1337, 1234, 1172, 1103, 768, 744, 588
    • +, 121.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.