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Volumn 4, Issue 7, 2012, Pages 963-967

Guanidine/Azole Binary System as an Efficient Catalyst for Morita-Baylis-Hillman Reaction

Author keywords

Azoles; Enantioselective; Guanidine; Morita Baylis Hillman reaction; Organocatalysis

Indexed keywords


EID: 84862735782     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200149     Document Type: Article
Times cited : (11)

References (59)
  • 4
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    • Offenlegungsschrift 2155113, U.S. Patent 3,743,669
    • A. B. Baylis, M. E. D. Hillman, Offenlegungsschrift 2155113, U.S. Patent 3, 743, 669, 1972; [ Chem. Abstr. 1972, 77, 34174q].
    • (1972) Chem. Abstr. , vol.77
    • Baylis, A.B.1    Hillman, M.E.D.2
  • 14
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    • For a review, see:
    • For a review, see:
  • 15
    • 70350474380 scopus 로고    scopus 로고
    • For selected recent examples of mechanistic investigations, see:
    • V. Carrasco-Sanchez, M. J. Simirgiotis, L. S. Santos, Molecules 2009, 14, 3989-4021. For selected recent examples of mechanistic investigations, see:
    • (2009) Molecules , vol.14 , pp. 3989-4021
    • Carrasco-Sanchez, V.1    Simirgiotis, M.J.2    Santos, L.S.3
  • 22
    • 84862733843 scopus 로고    scopus 로고
    • For the sole use of imidazole 4c as the promoter for the MBH reaction. For an equimolar amount, see:
    • For the sole use of imidazole 4c as the promoter for the MBH reaction. For an equimolar amount, see:
  • 26
    • 84862752413 scopus 로고    scopus 로고
    • For the use of azole derivatives 4 as a catalyst or catalytic system for the MBH reaction, see:
    • For the use of azole derivatives 4 as a catalyst or catalytic system for the MBH reaction, see:
  • 32
    • 84862752504 scopus 로고    scopus 로고
    • For the sole use of guanidine derivatives as the catalyst for the MBH reaction of acrylates. For TMG, see:
    • For the sole use of guanidine derivatives as the catalyst for the MBH reaction of acrylates. For TMG, see:
  • 36
    • 84862752411 scopus 로고    scopus 로고
    • The present binary catalytic system accelerated the reaction markedly in ethanol without exception of the typical MBH reaction. However considerable amounts of by-products were formed in this solvent. Other common organic solvents such as toluene and dichloromethane were applicable to the present system. The yields of the desired product 3aa were comparable to that observed in THF under the same reaction conditions using TMG/4d (Table1, entry4).
    • The present binary catalytic system accelerated the reaction markedly in ethanol without exception of the typical MBH reaction. However considerable amounts of by-products were formed in this solvent. Other common organic solvents such as toluene and dichloromethane were applicable to the present system. The yields of the desired product 3aa were comparable to that observed in THF under the same reaction conditions using TMG/4d (Table1, entry4).
  • 37
    • 84862752412 scopus 로고    scopus 로고
    • 2O, see:
    • 2O, see:
  • 54
    • 67649647843 scopus 로고    scopus 로고
    • For a personal research account, see:
    • H. Ube, M. Terada, Bioorg. Med. Chem. Lett. 2009, 19, 3895-3898. For a personal research account, see:
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3895-3898
    • Ube, H.1    Terada, M.2
  • 56
    • 84862733848 scopus 로고    scopus 로고
    • For reviews of chiral guanidine catalysts, see:
    • For reviews of chiral guanidine catalysts, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.