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Volumn 71, Issue 9, 2006, Pages 3506-3511

Synthesis of trifluoro- or difluoromethylated olefins by regio- and stereocontrolled SN2′ reactions of gem-difluorinated vinyloxiranes

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOLS; DIFLUOROMETHYLATED OLEFINS; GEM-DIFLUORINATED VINYLOXIRANES;

EID: 33646251418     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060089c     Document Type: Article
Times cited : (6)

References (78)
  • 3
    • 33646243517 scopus 로고    scopus 로고
    • Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds. ACS Symp. Ser. No. 639; American Chemical Society: Washington, DC
    • (a) Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symp. Ser. No. 639; American Chemical Society: Washington, DC, 1996.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
  • 6
    • 0029655531 scopus 로고    scopus 로고
    • The trifluoromethyl group is often claimed to be at least as large as the isopropyl group, see: (a) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99.
    • (1996) Tetrahedron , vol.52 , pp. 99
    • Schlosser, M.1    Michel, D.2
  • 15
    • 33646231696 scopus 로고    scopus 로고
    • Ramachandran, P. V., Ed. ACS Symp. Ser. No. 746; American Chemical Society: Washington, DC
    • (a) Ramachandran, P. V., Ed. Asymmetric Fluoroorganic Chemistry; ACS Symp. Ser. No. 746; American Chemical Society: Washington, DC, 2000.
    • (2000) Asymmetric Fluoroorganic Chemistry
  • 25
    • 0029655869 scopus 로고    scopus 로고
    • Preparations of them by Wittig-type olefination sometimes encounter serious disadvantage in terms of olefinic stereochemistry. See: Dolence, J. M.; Poulter, C. D. Tetrahedron 1996, 52, 119.
    • (1996) Tetrahedron , vol.52 , pp. 119
    • Dolence, J.M.1    Poulter, C.D.2
  • 26
    • 1842536055 scopus 로고    scopus 로고
    • In the preparation of them by a transition metal catalyzed cross-coupling reaction, the olefinic stereochemistries were excellent, but in some cases the regioselectivity is not perfect, moreover, quite a few examples of difluoromethylated olefins are described. See: (a) Konno, T.; Chae, J.; Tanaka, T.; Ishihara, T.; Yamanaka, H. Chem. Commun. 2004, 690.
    • (2004) Chem. Commun. , pp. 690
    • Konno, T.1    Chae, J.2    Tanaka, T.3    Ishihara, T.4    Yamanaka, H.5
  • 34
    • 0001720027 scopus 로고
    • N2′ reactions of gem-difluoroallylic alcohols by DAST were reported, see: Tellier, F.; Sauvêtre, R. J. Fluorine Chem. 1993, 62, 183.
    • (1993) Fluorine Chem. , vol.62 , pp. 183
    • Tellier, F.1    Sauvêtre, R.J.2
  • 47
    • 0344451115 scopus 로고
    • Amine-HF are known to react with nonfluorinated vinyloxiranes to afford vic-fluorohydrines, see: (a) Hedhli, A.; Baklouti, A. J. Fluorine Chem. 1995, 70, 141.
    • (1995) J. Fluorine Chem. , vol.70 , pp. 141
    • Hedhli, A.1    Baklouti, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.