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Volumn , Issue 42, 2006, Pages 4425-4427

5-endo Heck-type cyclization of 2-(trifluoromethyl)allyl ketone oximes: Synthesis of 4-difluoromethylene-substituted 1-pyrrolines

Author keywords

[No Author keywords available]

Indexed keywords

2 TRIFLUOROMETHYLALLYLKETONE OXIME DERIVATIVE; 4 DIFLUOROMETHYLENE 1 PYRROLINE; ALKENE; OXIME DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33750268103     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b610690k     Document Type: Article
Times cited : (104)

References (44)
  • 7
    • 1442286435 scopus 로고    scopus 로고
    • For recent examples of difluoromethylene-substituted pyrrolidines, see:
    • X.-L. Qiu F.-L. Qing Synthesis 2004 334.
    • (2004) Synthesis , pp. 334
    • Qiu, X.-L.1    Qing, F.-L.2
  • 9
    • 0037019959 scopus 로고    scopus 로고
    • For recent examples of monofluoromethyl-substituted pyrrolidines, see:
    • X.-L. Qiu F.-L. Qing J. Org. Chem. 2002 67 7162
    • (2002) J. Org. Chem. , vol.67 , pp. 7162
    • Qiu, X.-L.1    Qing, F.-L.2
  • 17
    • 33750279624 scopus 로고    scopus 로고
    • The reaction was conducted on treatment of 3-trifluoromethyl-2,2- dimethyl-1-phenylbut-3-en-1-imine with 1.3 equivalents of NaH in N,N-dimethylformamide (DMF). The reaction mixture was stirred at 0°C for 20 min and then heated at 90°C for 1.5 h to give 4-difluoromethyl-3,3-dimethyl- 2-phenyl-3H-pyrrole (9%) with decomposition of the starting imine
    • The reaction was conducted on treatment of 3-trifluoromethyl-2,2- dimethyl-1-phenylbut-3-en-1-imine with 1.3 equivalents of NaH in N,N-dimethylformamide (DMF). The reaction mixture was stirred at 0°C for 20 min and then heated at 90°C for 1.5 h to give 4-difluoromethyl-3,3-dimethyl- 2-phenyl-3H-pyrrole (9%) with decomposition of the starting imine
  • 18
    • 0038322529 scopus 로고    scopus 로고
    • Most of the studies on Heck cyclizations in a 5-endo fashion dealt with substrates bearing an enamine (or its equivalent) moiety, which can be interpreted in terms of a mechanism other than a 5-endo cyclization, involving: (i) the oxidative addition of aryl or alkenyl halides to Pd(0), (ii) the formation of six-membered palladacycles through nucleophilic substitution with the enamine on the palladium and (iii) a subsequent reductive elimination, which leads to the 5-endo type products. For recent examples, see:
    • M. Kitamura K. Narasaka Chem. Rec. 2002 2 268
    • (2002) Chem. Rec. , vol.2 , pp. 268
    • Kitamura, M.1    Narasaka, K.2
  • 24
    • 0034697488 scopus 로고    scopus 로고
    • 5-endo Cyclizations of aryl- and alkenylpalladiums are less efficient.
    • R. Grigg V. Savic Chem. Commun. 2000 873
    • (2000) Chem. Commun. , pp. 873
    • Grigg, R.1    Savic, V.2
  • 27
    • 0001345564 scopus 로고
    • 5-endo Cyclizations of acylpalladiums are originally reported by Negishi and modified by Larock.
    • B. O'Connor Y. Zhang E. Negishi Tetrahedron Lett. 1988 29 3903
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3903
    • O'Connor, B.1    Zhang, Y.2    Negishi, E.3
  • 35
    • 84989726030 scopus 로고
    • Regiochemistry in intermolecular Heck reaction of 3,3,3-trifluoropropene was explained by DFT calculations, see:
    • T. Fuchikami M. Yatabe I. Ojima Synthesis 1981 365.
    • (1981) Synthesis , pp. 365
    • Fuchikami, T.1    Yatabe, M.2    Ojima, I.3
  • 43
    • 0036501275 scopus 로고    scopus 로고
    • For a recent review on the gem-dialkyl effect, see:
    • V. V. Grushin Chem.-Eur. J. 2002 8 1006
    • (2002) Chem.-Eur. J. , vol.8 , pp. 1006
    • Grushin, V.V.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.