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Volumn 44, Issue 7, 1996, Pages 1314-1317

Diastereoselective (ethoxycarbonyl)difluoromethylation of chiral imide enolates mediated by triethylborane

Author keywords

(ethoxycarbonyl)difluoromethylation; asymmetric synthesis; chiral fluorinated compound; ethyl difluoroiodoacetate; N acyloxazolidinone; triethylborane

Indexed keywords

ACETIC ACID DERIVATIVE; BORANE DERIVATIVE; IMIDE; LITHIUM DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

EID: 0030017449     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1314     Document Type: Article
Times cited : (8)

References (23)
  • 1
    • 0003420735 scopus 로고
    • Kodansha Ltd. and Elsevier Biomedical Press, Tokyo and Amsterdam
    • "Biomedical Aspects of Fluorine Chemistry," ed. by Filler R., Kobayashi Y., Kodansha Ltd. and Elsevier Biomedical Press, Tokyo and Amsterdam, 1982; Welch J. T., Tetrahedron, 43, 3123 (1987); Welch J. T., Eswarakrishnan S., "Fluorine in Bioorganic Chemistry," John Wiley & Sons, New York, 1991; "Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications," ed. by Filler R., Kobayashi Y., Yagupolskii L. M., Elsevier, Amsterdam, 1993.
    • (1982) Biomedical Aspects of Fluorine Chemistry
    • Filler, R.1    Kobayashi, Y.2
  • 2
    • 0023237559 scopus 로고
    • "Biomedical Aspects of Fluorine Chemistry," ed. by Filler R., Kobayashi Y., Kodansha Ltd. and Elsevier Biomedical Press, Tokyo and Amsterdam, 1982; Welch J. T., Tetrahedron, 43, 3123 (1987); Welch J. T., Eswarakrishnan S., "Fluorine in Bioorganic Chemistry," John Wiley & Sons, New York, 1991; "Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications," ed. by Filler R., Kobayashi Y., Yagupolskii L. M., Elsevier, Amsterdam, 1993.
    • (1987) Tetrahedron , vol.43 , pp. 3123
    • Welch, J.T.1
  • 3
    • 0003907264 scopus 로고
    • John Wiley & Sons, New York
    • "Biomedical Aspects of Fluorine Chemistry," ed. by Filler R., Kobayashi Y., Kodansha Ltd. and Elsevier Biomedical Press, Tokyo and Amsterdam, 1982; Welch J. T., Tetrahedron, 43, 3123 (1987); Welch J. T., Eswarakrishnan S., "Fluorine in Bioorganic Chemistry," John Wiley & Sons, New York, 1991; "Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications," ed. by Filler R., Kobayashi Y., Yagupolskii L. M., Elsevier, Amsterdam, 1993.
    • (1991) Fluorine in Bioorganic Chemistry
    • Welch, J.T.1    Eswarakrishnan, S.2
  • 4
    • 0003490830 scopus 로고
    • Elsevier, Amsterdam
    • "Biomedical Aspects of Fluorine Chemistry," ed. by Filler R., Kobayashi Y., Kodansha Ltd. and Elsevier Biomedical Press, Tokyo and Amsterdam, 1982; Welch J. T., Tetrahedron, 43, 3123 (1987); Welch J. T., Eswarakrishnan S., "Fluorine in Bioorganic Chemistry," John Wiley & Sons, New York, 1991; "Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications," ed. by Filler R., Kobayashi Y., Yagupolskii L. M., Elsevier, Amsterdam, 1993.
    • (1993) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications
    • Filler, R.1    Kobayashi, Y.2    Yagupolskii, L.M.3
  • 6
    • 0000532882 scopus 로고
    • Bravo P., Resnati G., Tetrahedron: Asymmetry, 1, 661 (1990); Resnati G., Tetrahedron, 49, 9385 (1993); Iseki K., Kobayashi Y., Yuki Goxei Kagaku Kyokai Shi, 52, 40 (1994); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by Hayashi T., Soloshonok V. A. (guest Eds.), Tetrahedron: Asymmetry, 5, 955 (1994).
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 661
    • Bravo, P.1    Resnati, G.2
  • 7
    • 0027432004 scopus 로고
    • Bravo P., Resnati G., Tetrahedron: Asymmetry, 1, 661 (1990); Resnati G., Tetrahedron, 49, 9385 (1993); Iseki K., Kobayashi Y., Yuki Goxei Kagaku Kyokai Shi, 52, 40 (1994); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by Hayashi T., Soloshonok V. A. (guest Eds.), Tetrahedron: Asymmetry, 5, 955 (1994).
    • (1993) Tetrahedron , vol.49 , pp. 9385
    • Resnati, G.1
  • 8
    • 0027962165 scopus 로고
    • Bravo P., Resnati G., Tetrahedron: Asymmetry, 1, 661 (1990); Resnati G., Tetrahedron, 49, 9385 (1993); Iseki K., Kobayashi Y., Yuki Goxei Kagaku Kyokai Shi, 52, 40 (1994); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by Hayashi T., Soloshonok V. A. (guest Eds.), Tetrahedron: Asymmetry, 5, 955 (1994).
    • (1994) Yuki Goxei Kagaku Kyokai Shi , vol.52 , pp. 40
    • Iseki, K.1    Kobayashi, Y.2
  • 9
    • 0001101736 scopus 로고
    • Enantiocontrolled Synthesis of Fluoro-Organic Compounds
    • Bravo P., Resnati G., Tetrahedron: Asymmetry, 1, 661 (1990); Resnati G., Tetrahedron, 49, 9385 (1993); Iseki K., Kobayashi Y., Yuki Goxei Kagaku Kyokai Shi, 52, 40 (1994); "Enantiocontrolled Synthesis of Fluoro-Organic Compounds," ed. by Hayashi T., Soloshonok V. A. (guest Eds.), Tetrahedron: Asymmetry, 5, 955 (1994).
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 955
    • Hayashi, T.1    Soloshonok, V.A.2
  • 14
    • 0000744779 scopus 로고
    • Evans D. A., Britton T. C., Dorow R. L., Dellaria J. F., Tetrahedron, 44, 5525 (1988); Gage J. R., Evans D. A., Org. Synth., 68, 77 (1989); idem, ibid., 68, 83 (1989).
    • (1989) Org. Synth. , vol.68 , pp. 77
    • Gage, J.R.1    Evans, D.A.2
  • 15
    • 0000744779 scopus 로고
    • Evans D. A., Britton T. C., Dorow R. L., Dellaria J. F., Tetrahedron, 44, 5525 (1988); Gage J. R., Evans D. A., Org. Synth., 68, 77 (1989); idem, ibid., 68, 83 (1989).
    • (1989) Org. Synth. , vol.68 , pp. 83
    • Gage, J.R.1    Evans, D.A.2
  • 16
    • 33751500754 scopus 로고
    • Ethyl difluoroiodoacetate was prepared from ethyl bromodifluoro-acetate according to Yang Z.-Y., Burton D. J., J. Org. Chem., 56, 5125 (1991).
    • (1991) J. Org. Chem. , vol.56 , pp. 5125
    • Yang, Z.-Y.1    Burton, D.J.2
  • 17
    • 0001002609 scopus 로고
    • Patrick T. B., Johri K. K., White D. H., J. Org. Chem., 48, 4158 (1983); Patrick T. B., Johri K. K., White D. H., Bertrand W. S., Rokhtar R., Kilbourn M. R., Welch M. J., Can. J. Chem., 64, 138 (1986).
    • (1983) J. Org. Chem. , vol.48 , pp. 4158
    • Patrick, T.B.1    Johri, K.K.2    White, D.H.3
  • 23
    • 9344238327 scopus 로고    scopus 로고
    • note
    • The (ethoxycarbonyl)difluoromethylation may possibly not require the generation of stoichiometric amounts of ethyl radical, since a catalytic amount of oxygen in argon, solvents and reagents can activate only a small amount of triethylborane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.