Asymmetric Synthesis of Unsaturated Pipecolic Acid Derivatives

Synlett

Volumn 1997, Issue 7, 1997, Pages 799-800

  Agami, Claude ^a   Bihan, Dominique ^a   Morgentin, Rémy ^a   Puchot Kadouri, Cathy ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003051647     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5752     Document Type: Article

References (23)

1. Duthaler R.O. Tetrahedron, 1994, 50, 1539.
2. See, for recent examples: Jackson, R.F.W.; Graham, L.J.; Rettie, A.B. Tetrahedron Lett., 1994, 35, 4417; Berrien, J.F.; Royer, J.; Husson, H.P. J. Org. Chem., 1994, 59, 3769; Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett., 1995, 36, 2037; Davies, C.E.; Heightman, T. D.; Hermitage, S.A; Moloney, M.G. Synth. Commun., 1996, 26, 687; Agami, C.; Couty, F.; Mathieu, H, Tetrahedron Lett., 1996, 37, 4001.
3. See, for recent examples: Jackson, R.F.W.; Graham, L.J.; Rettie, A.B. Tetrahedron Lett., 1994, 35, 4417; Berrien, J.F.; Royer, J.; Husson, H.P. J. Org. Chem., 1994, 59, 3769; Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett., 1995, 36, 2037; Davies, C.E.; Heightman, T. D.; Hermitage, S.A; Moloney, M.G. Synth. Commun., 1996, 26, 687; Agami, C.; Couty, F.; Mathieu, H, Tetrahedron Lett., 1996, 37, 4001.
4. See, for recent examples: Jackson, R.F.W.; Graham, L.J.; Rettie, A.B. Tetrahedron Lett., 1994, 35, 4417; Berrien, J.F.; Royer, J.; Husson, H.P. J. Org. Chem., 1994, 59, 3769; Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett., 1995, 36, 2037; Davies, C.E.; Heightman, T. D.; Hermitage, S.A; Moloney, M.G. Synth. Commun., 1996, 26, 687; Agami, C.; Couty, F.; Mathieu, H, Tetrahedron Lett., 1996, 37, 4001.
5. See, for recent examples: Jackson, R.F.W.; Graham, L.J.; Rettie, A.B. Tetrahedron Lett., 1994, 35, 4417; Berrien, J.F.; Royer, J.; Husson, H.P. J. Org. Chem., 1994, 59, 3769; Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett., 1995, 36, 2037; Davies, C.E.; Heightman, T. D.; Hermitage, S.A; Moloney, M.G. Synth. Commun., 1996, 26, 687; Agami, C.; Couty, F.; Mathieu, H, Tetrahedron Lett., 1996, 37, 4001.
6. See, for recent examples: Jackson, R.F.W.; Graham, L.J.; Rettie, A.B. Tetrahedron Lett., 1994, 35, 4417; Berrien, J.F.; Royer, J.; Husson, H.P. J. Org. Chem., 1994, 59, 3769; Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett., 1995, 36, 2037; Davies, C.E.; Heightman, T. D.; Hermitage, S.A; Moloney, M.G. Synth. Commun., 1996, 26, 687; Agami, C.; Couty, F.; Mathieu, H, Tetrahedron Lett., 1996, 37, 4001.
7. 4-unsaturated (S)-pipecolic acid, see: Fujita, Y.; Irrevere, F.; Witcop, B. J. Am. Chem. Soc., 1964, 86, 1844; Callens, R.E.A.; Anteunis, M.J.O, Bull. Soc. Chim. Belg., 1982, 91, 713; Hanson, G.J.; Russel, M.A. Tetrahedron Lett., 1989, 30, 5751.
8. 4-unsaturated (S)-pipecolic acid, see: Fujita, Y.; Irrevere, F.; Witcop, B. J. Am. Chem. Soc., 1964, 86, 1844; Callens, R.E.A.; Anteunis, M.J.O, Bull. Soc. Chim. Belg., 1982, 91, 713; Hanson, G.J.; Russel, M.A. Tetrahedron Lett., 1989, 30, 5751.
9. 4-unsaturated (S)-pipecolic acid, see: Fujita, Y.; Irrevere, F.; Witcop, B. J. Am. Chem. Soc., 1964, 86, 1844; Callens, R.E.A.; Anteunis, M.J.O, Bull. Soc. Chim. Belg., 1982, 91, 713; Hanson, G.J.; Russel, M.A. Tetrahedron Lett., 1989, 30, 5751.
10. Ojima, I.; Tzamarioudaki. M.; Egushi, M. J. Org. Chem., 1995, 60, 7078.
11. Baldwin, J.E.; Flinn, A. Tetrahedron Lett., 1987, 28, 3605; Browterman, Q.B.; Kaptein B.; Kamphuis, J.; Schoemaker, H.E. J. Org. Chem., 1992, 57, 6286; Baumann, H.; Duthaler, R. Helv. Chim. Acta. 1988, 71, 1025.
12. Baldwin, J.E.; Flinn, A. Tetrahedron Lett., 1987, 28, 3605; Browterman, Q.B.; Kaptein B.; Kamphuis, J.; Schoemaker, H.E. J. Org. Chem., 1992, 57, 6286; Baumann, H.; Duthaler, R. Helv. Chim. Acta. 1988, 71, 1025.
13. Baldwin, J.E.; Flinn, A. Tetrahedron Lett., 1987, 28, 3605; Browterman, Q.B.; Kaptein B.; Kamphuis, J.; Schoemaker, H.E. J. Org. Chem., 1992, 57, 6286; Baumann, H.; Duthaler, R. Helv. Chim. Acta. 1988, 71, 1025.
14. Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett., 1983, 24, 1407; Esch, P.M.; Boska, I.M.; Hiemstra, H.; de Boer, R.F.; Speckamp, W.N. Tetrahedron, 1991, 47, 4039; see also: Tietze, L.F.; Bratz, M. Synthesis, 1989, 439.
15. Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett., 1983, 24, 1407; Esch, P.M.; Boska, I.M.; Hiemstra, H.; de Boer, R.F.; Speckamp, W.N. Tetrahedron, 1991, 47, 4039; see also: Tietze, L.F.; Bratz, M. Synthesis, 1989, 439.
16. Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett., 1983, 24, 1407; Esch, P.M.; Boska, I.M.; Hiemstra, H.; de Boer, R.F.; Speckamp, W.N. Tetrahedron, 1991, 47, 4039; see also: Tietze, L.F.; Bratz, M. Synthesis, 1989, 439.
17. Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron, 1996, 52, 9079.
18. Hiemstra, H.; Sno, M.H.A.M; Vijn, R.J.; Speckamp, W.N. J. Org. Chem., 1985, 50, 4014.
19. 1H DIFNOE NMR (250 MHz) data of intermediate lactone 7 are as follows: (Matrix Presented)
20. 2O): 30.8, 34.5, 45.6, 54.9, 58.5, 114.9, 139.0, 170.7.
21. Miguel, D.; Diez, A.; Blache, Y.; Luque, J.; Orozco, M.; Remuson, R.; Gelas-Mialhe, Y.; Rubiralta, M. Tetrahedron, 1995, 51, 7527.
22. D: -18 (c 1, 2N HCl)].
23. Okamoto, S.; Hijikata, A.; Kikumoto, R.; Tonomura, S.; Hara, H.; Ninomiya, K.; Maruyama, A.; Sugano, M.; Tamao, Y. Biochem. Biophys. Res. Commun., 1981, 101, 440.