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Volumn , Issue 2, 1998, Pages 119-120

Stereospecific reduction with retention of chiral fluoral-derived 1,3-oxazolidines with LiAlH4 : Asymmetric synthesis of 1-substituted 2,2,2-trifluoroethylamines

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EID: 0032387023     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.119     Document Type: Article
Times cited : (25)

References (31)
  • 1
    • 0003481072 scopus 로고    scopus 로고
    • Wiley, Chichester
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1998) Reviews: "Enantiocontrolled Synthesis of Fluoro-organic Compounds: Stereochemical Challenges and Biomedical Targets,"
    • Soloshonok, V.A.1
  • 2
    • 0001834676 scopus 로고    scopus 로고
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1996) Tetrahedron , vol.52 , pp. 1
    • Resnati, G.1    Soloshonok, V.A.2
  • 3
    • 0030082349 scopus 로고    scopus 로고
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1996) J. Synth. Org. Chem., Jpn. , vol.54 , pp. 122
    • Iseki, K.1    Kobayashi, Y.2
  • 4
    • 0001101736 scopus 로고
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 955
    • Hayashi, T.1    Soloshonok, V.A.2
  • 5
    • 0027432004 scopus 로고
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1993) Tetrahedron , vol.49 , pp. 9385
    • Resnati, G.1
  • 6
    • 0010634352 scopus 로고
    • Kodansha Scientific, Tokyo
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1993) Fluorine Chemistry
    • Kitazume, T.1    Ishihara, T.2    Taguchi, T.3
  • 7
    • 0004185069 scopus 로고
    • Wiley, N.Y.
    • Reviews: "Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets," ed by V. A. Soloshonok, Wiley, Chichester (1998); G. Resnati and V. A. Soloshonok, Tetrahedron, 52, 1 (1996); K. Iseki and Y. Kobayashi, J. Synth. Org. Chem., Jpn., 54, 122 (1996); T. Hayashi and V. A. Soloshonok, Tetrahedron: Asymmetry, 5, 955 (1994); G. Resnati, Tetrahedron, 49, 9385 (1993); T. Kitazume, T. Ishihara, and T. Taguchi, "Fluorine Chemistry," Kodansha Scientific, Tokyo (1993); G. A. Olah, R. D. Chambers, and G. K. S. Prakash, "Synthetic Fluorine Chemistry," Wiley, N.Y. (1992).
    • (1992) Synthetic Fluorine Chemistry
    • Olah, G.A.1    Chambers, R.D.2    Prakash, G.K.S.3
  • 8
    • 0041715029 scopus 로고    scopus 로고
    • E. Patent 297752A2 (1989).
    • In the reaction of fluorinated compounds, lower degree or opposite sense of stereoselectivity were observed in comparison with nonfluorinated counterparts: a) N. Sayo, T. Saito, S. Akutagawa, R. Noyori, and H. Takaya, E. Patent 297752A2 (1989).
    • Sayo, N.1    Saito, T.2    Akutagawa, S.3    Noyori, R.4    Takaya, H.5
  • 14
    • 0001130169 scopus 로고
    • Previous reports on the preparation of chiral 1-substituted 2,2,2-trifluoroethylamines: a) Asymmetric reduction of chiral imine: W. H. Pirkle and J. R. Hauske, J. Org. Chem., 42, 2436 (1977).
    • (1977) J. Org. Chem. , vol.42 , pp. 2436
    • Pirkle, W.H.1    Hauske, J.R.2
  • 18
    • 0041715028 scopus 로고    scopus 로고
    • note
    • 2 to give benzyl imine product (4) (43% yield). The geometry of chiral imine (4) was deduced to be E from the result of X-ray analysis of a similar (R)-1-trifluoromethyl-N-(2-hydroxy-1-phenylethyl)benzylideneamine.
  • 25
    • 0343884377 scopus 로고    scopus 로고
    • Abstr., 1G201 Tokyo
    • b) H. Matsutani, J. Yaruva, H. Poras, T. Kusumoto, and T. Hiyama, Abstr., B109 in the 44th Symposium on Organometallic Chemistry of the Kinki Chemical Society, Osaka, Japan, 1997. H. Matsutani, T. Kusumoto, and T. Hiyama, Abstr., 1G201 in the 72th Annual Meeting of the Chemical Society of Japan, Tokyo, 1997. For the mechanism on the Lewis acid-catalyzed nucleophilic substitution of nonfluorinated acetals, see:
    • (1997) 72th Annual Meeting of the Chemical Society of Japan
    • Matsutani, H.1    Kusumoto, T.2    Hiyama, T.3
  • 31
    • 0042215428 scopus 로고    scopus 로고
    • by Pd-C: Ref. 4a
    • b) Hydrogenolysis by Pd-C: Ref. 4a.
    • Hydrogenolysis


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