Versatile synthesis of enantiomerically pure trans-2,5-disubstituted pyrrolidines

Heterocycles

Volumn 42, Issue 2, 1996, Pages 529-532

  Dockner, Michael ^a   Sasaki, N André ^a   Potier, Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001469816     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s89     Document Type: Article

References (18)

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3. Y. Ito, T. Katsuki, and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 6017; S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, and M. Yamaguchi, Tetrahedron, 1988, 44, 5333 and references therein; L. Ghosez, C. Genicot, and V. Gouverneur, Pure and Appl. Chem., 1992, 64, 1849; C. Genicot and L.Ghosez, Tetrahedron Lett., 1992, 33, 7357; N. A. Porter, E. Swann, J. Nally, and A. T. McPhail, J. Amer. Chem. Soc., 1990, 112, 6740 and references therein; O. Kitagawa, T. Hanano, N. Kikuchi, and T. Taguchi, Tetrahedron Lett., 1993, 34, 2165; B. Giese, U. Hoffmann, M. Rhoth, A. Veit, C. Wyss, M. Zehnder, and H. Zipse, Tetrahedron Lett., 1993, 34, 2445; K. Koh, R. N. Ben, and T. Durst, Tetrahedron Lett., 1994, 35, 375; M. P. Sibi and J.-L. Lu, Tetrahedron Lett., 1994, 35, 4915; W. Oppolzer, C. G. Bochet, and E. Merifield, Tetrahedron Lett., 1994, 35, 7015; K. Higashigawa, H. Inoue, and H. Takahashi, Tetrahedron, 1994, 50, 1083; R. Bloch, C. Brillet-Fernandez, and J. Mandville, Tetrahedron: Asymmetry, 1994, 5, 745.
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5. Y. Ito, T. Katsuki, and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 6017; S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, and M. Yamaguchi, Tetrahedron, 1988, 44, 5333 and references therein; L. Ghosez, C. Genicot, and V. Gouverneur, Pure and Appl. Chem., 1992, 64, 1849; C. Genicot and L.Ghosez, Tetrahedron Lett., 1992, 33, 7357; N. A. Porter, E. Swann, J. Nally, and A. T. McPhail, J. Amer. Chem. Soc., 1990, 112, 6740 and references therein; O. Kitagawa, T. Hanano, N. Kikuchi, and T. Taguchi, Tetrahedron Lett., 1993, 34, 2165; B. Giese, U. Hoffmann, M. Rhoth, A. Veit, C. Wyss, M. Zehnder, and H. Zipse, Tetrahedron Lett., 1993, 34, 2445; K. Koh, R. N. Ben, and T. Durst, Tetrahedron Lett., 1994, 35, 375; M. P. Sibi and J.-L. Lu, Tetrahedron Lett., 1994, 35, 4915; W. Oppolzer, C. G. Bochet, and E. Merifield, Tetrahedron Lett., 1994, 35, 7015; K. Higashigawa, H. Inoue, and H. Takahashi, Tetrahedron, 1994, 50, 1083; R. Bloch, C. Brillet-Fernandez, and J. Mandville, Tetrahedron: Asymmetry, 1994, 5, 745.
6. Y. Ito, T. Katsuki, and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 6017; S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, and M. Yamaguchi, Tetrahedron, 1988, 44, 5333 and references therein; L. Ghosez, C. Genicot, and V. Gouverneur, Pure and Appl. Chem., 1992, 64, 1849; C. Genicot and L.Ghosez, Tetrahedron Lett., 1992, 33, 7357; N. A. Porter, E. Swann, J. Nally, and A. T. McPhail, J. Amer. Chem. Soc., 1990, 112, 6740 and references therein; O. Kitagawa, T. Hanano, N. Kikuchi, and T. Taguchi, Tetrahedron Lett., 1993, 34, 2165; B. Giese, U. Hoffmann, M. Rhoth, A. Veit, C. Wyss, M. Zehnder, and H. Zipse, Tetrahedron Lett., 1993, 34, 2445; K. Koh, R. N. Ben, and T. Durst, Tetrahedron Lett., 1994, 35, 375; M. P. Sibi and J.-L. Lu, Tetrahedron Lett., 1994, 35, 4915; W. Oppolzer, C. G. Bochet, and E. Merifield, Tetrahedron Lett., 1994, 35, 7015; K. Higashigawa, H. Inoue, and H. Takahashi, Tetrahedron, 1994, 50, 1083; R. Bloch, C. Brillet-Fernandez, and J. Mandville, Tetrahedron: Asymmetry, 1994, 5, 745.
7. Y. Ito, T. Katsuki, and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 6017; S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, and M. Yamaguchi, Tetrahedron, 1988, 44, 5333 and references therein; L. Ghosez, C. Genicot, and V. Gouverneur, Pure and Appl. Chem., 1992, 64, 1849; C. Genicot and L.Ghosez, Tetrahedron Lett., 1992, 33, 7357; N. A. Porter, E. Swann, J. Nally, and A. T. McPhail, J. Amer. Chem. Soc., 1990, 112, 6740 and references therein; O. Kitagawa, T. Hanano, N. Kikuchi, and T. Taguchi, Tetrahedron Lett., 1993, 34, 2165; B. Giese, U. Hoffmann, M. Rhoth, A. Veit, C. Wyss, M. Zehnder, and H. Zipse, Tetrahedron Lett., 1993, 34, 2445; K. Koh, R. N. Ben, and T. Durst, Tetrahedron Lett., 1994, 35, 375; M. P. Sibi and J.-L. Lu, Tetrahedron Lett., 1994, 35, 4915; W. Oppolzer, C. G. Bochet, and E. Merifield, Tetrahedron Lett., 1994, 35, 7015; K. Higashigawa, H. Inoue, and H. Takahashi, Tetrahedron, 1994, 50, 1083; R. Bloch, C. Brillet-Fernandez, and J. Mandville, Tetrahedron: Asymmetry, 1994, 5, 745.
8. Y. Ito, T. Katsuki, and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 6017; S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, and M. Yamaguchi, Tetrahedron, 1988, 44, 5333 and references therein; L. Ghosez, C. Genicot, and V. Gouverneur, Pure and Appl. Chem., 1992, 64, 1849; C. Genicot and L.Ghosez, Tetrahedron Lett., 1992, 33, 7357; N. A. Porter, E. Swann, J. Nally, and A. T. McPhail, J. Amer. Chem. Soc., 1990, 112, 6740 and references therein; O. Kitagawa, T. Hanano, N. Kikuchi, and T. Taguchi, Tetrahedron Lett., 1993, 34, 2165; B. Giese, U. Hoffmann, M. Rhoth, A. Veit, C. Wyss, M. Zehnder, and H. Zipse, Tetrahedron Lett., 1993, 34, 2445; K. Koh, R. N. Ben, and T. Durst, Tetrahedron Lett., 1994, 35, 375; M. P. Sibi and J.-L. Lu, Tetrahedron Lett., 1994, 35, 4915; W. Oppolzer, C. G. Bochet, and E. Merifield, Tetrahedron Lett., 1994, 35, 7015; K. Higashigawa, H. Inoue, and H. Takahashi, Tetrahedron, 1994, 50, 1083; R. Bloch, C. Brillet-Fernandez, and J. Mandville, Tetrahedron: Asymmetry, 1994, 5, 745.
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17. 6 by treatment with benzyl bromide in DMF in the presence of 1 eq. of NaH at 0 °C; (A)-2,3-O-isopropylideneglycerol with 99% e.e. was purchased from CHEMI S.p.A, Cinisello Balsamo, Italy.
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