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Volumn 133, Issue 6, 2011, Pages 1650-1653

Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles

Author keywords

[No Author keywords available]

Indexed keywords

C-H FUNCTIONALIZATION; CARBENES; CATALYTIC AMOUNTS; DFT CALCULATION; DIAZO COMPOUNDS; ENANTIOSELECTIVE; HIGH YIELD; OXOCARBENIUM;

EID: 79951542336     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1093309     Document Type: Article
Times cited : (167)

References (44)
  • 4
    • 77955673540 scopus 로고    scopus 로고
    • For medicinally active indol-3-yl acetate derivatives with stereocenters α to C3, see:
    • Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489
    • (2010) Chem. Rev. , vol.110 , pp. 4489
    • Kochanowska-Karamyan, A.J.1    Hamann, M.T.2
  • 37
    • 84862767082 scopus 로고    scopus 로고
    • Known substrate limitations: indole with ethyl α-diazobutanoate gave the product of N-H insertion in 29% yield and <1% ee; 6-(hydroxymethyl)- N -methylindole with ethyl α-diazo-5-methylhexanoate gave the product of O-H insertion in 41% yield and <1% ee; 1,2-dimethyl-6-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-1 H -indole with ethyl α-diazo-5-methylhexanoate gave the desired C-H functionalization product in 81% yield, but only 13% ee; 5-nitro-1,2-dimethylindole with ethyl α-diazobutanoate did not give any intermolecular products.
    • Known substrate limitations: indole with ethyl α-diazobutanoate gave the product of N-H insertion in 29% yield and <1% ee; 6-(hydroxymethyl)- N -methylindole with ethyl α-diazo-5-methylhexanoate gave the product of O-H insertion in 41% yield and <1% ee; 1,2-dimethyl-6-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-1 H -indole with ethyl α-diazo-5-methylhexanoate gave the desired C-H functionalization product in 81% yield, but only 13% ee; 5-nitro-1,2-dimethylindole with ethyl α-diazobutanoate did not give any intermolecular products.
  • 38
    • 79951539357 scopus 로고    scopus 로고
    • For the preparation of 16 and 17, it was important to use only 1 equiv of diazoester. Enantioselectivity was lower and difficult to reproduce when 2 equiv of diazoester was used. Azine side products (7c) were formed when excess amounts of diazoesters were employed. We believe that the azine acts as a base that epimerizes 16 and 17.
    • For the preparation of 16 and 17, it was important to use only 1 equiv of diazoester. Enantioselectivity was lower and difficult to reproduce when 2 equiv of diazoester was used. Azine side products (7c) were formed when excess amounts of diazoesters were employed. We believe that the azine acts as a base that epimerizes 16 and 17.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.