Pyrrolidinic and piperidinic ring fission by conjugate elimination

Tetrahedron Letters

Volumn 43, Issue 48, 2002, Pages 8759-8763

  Acquadro, Francesco ^a,b   Oulyadi, Hassan ^a   Venturello, Paolo ^b   Maddaluno, Jacques ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BASE; CATION; FUNCTIONAL GROUP; NITROGEN; PIPERIDINE DERIVATIVE; PYRROLINE DERIVATIVE; SOLVENT;

ALPHA CHAIN; ARTICLE; CHELATION; CHEMICAL MODIFICATION; PROTON TRANSPORT;

EID: 0037175467     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02155-X     Document Type: Article

References (33)

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4. Inter alia: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258; (b) Husson, H.-P.; Royer J. Chem. Soc. Rev. 1999, 28, 383-394; (c) Tehrani, K. A.; Syngel, K. V.; Boelens, M. Contreras, J.; De Kimpe, N.; Knight D. W. Tetrahedron Lett. 2000, 41, 2507-2510; (d) Rougnon Glasson, S.; Canet, J.-L.; Troin, Y. Tetrahedron Lett. 2000, 41, 9797-9802.
5. Inter alia: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258; (b) Husson, H.-P.; Royer J. Chem. Soc. Rev. 1999, 28, 383-394; (c) Tehrani, K. A.; Syngel, K. V.; Boelens, M. Contreras, J.; De Kimpe, N.; Knight D. W. Tetrahedron Lett. 2000, 41, 2507-2510; (d) Rougnon Glasson, S.; Canet, J.-L.; Troin, Y. Tetrahedron Lett. 2000, 41, 9797-9802.
6. Inter alia: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258; (b) Husson, H.-P.; Royer J. Chem. Soc. Rev. 1999, 28, 383-394; (c) Tehrani, K. A.; Syngel, K. V.; Boelens, M. Contreras, J.; De Kimpe, N.; Knight D. W. Tetrahedron Lett. 2000, 41, 2507-2510; (d) Rougnon Glasson, S.; Canet, J.-L.; Troin, Y. Tetrahedron Lett. 2000, 41, 9797-9802.
7. Recent nitrogen heterocycles openings: (a) Frölich, K.; Wagemann, R.; Vilsmaier, E. Tetrahedron 1998, 54, 13115-13128; (b) Cocquet, G.; Ferroud, C.; Guy, A. Tetrahedron 2000, 56, 2975-2984; (c) Ishimaru, K.; Kojima, T. J. Org. Chem. 2000, 65, 8395-8398; (d) Neipp, C. E.; Humphrey, J. M.; Martin, S. F. J. Org. Chem. 2001, 66, 531-537.
8. Recent nitrogen heterocycles openings: (a) Frölich, K.; Wagemann, R.; Vilsmaier, E. Tetrahedron 1998, 54, 13115-13128; (b) Cocquet, G.; Ferroud, C.; Guy, A. Tetrahedron 2000, 56, 2975-2984; (c) Ishimaru, K.; Kojima, T. J. Org. Chem. 2000, 65, 8395-8398; (d) Neipp, C. E.; Humphrey, J. M.; Martin, S. F. J. Org. Chem. 2001, 66, 531-537.
9. Recent nitrogen heterocycles openings: (a) Frölich, K.; Wagemann, R.; Vilsmaier, E. Tetrahedron 1998, 54, 13115-13128; (b) Cocquet, G.; Ferroud, C.; Guy, A. Tetrahedron 2000, 56, 2975-2984; (c) Ishimaru, K.; Kojima, T. J. Org. Chem. 2000, 65, 8395-8398; (d) Neipp, C. E.; Humphrey, J. M.; Martin, S. F. J. Org. Chem. 2001, 66, 531-537.
10. Recent nitrogen heterocycles openings: (a) Frölich, K.; Wagemann, R.; Vilsmaier, E. Tetrahedron 1998, 54, 13115-13128; (b) Cocquet, G.; Ferroud, C.; Guy, A. Tetrahedron 2000, 56, 2975-2984; (c) Ishimaru, K.; Kojima, T. J. Org. Chem. 2000, 65, 8395-8398; (d) Neipp, C. E.; Humphrey, J. M.; Martin, S. F. J. Org. Chem. 2001, 66, 531-537.
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17. The reverse 5-exo trig addition of the lithium amide onto the dienic system should indeed be favored according to: (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-738; (b) Calaza, M. I.; Paleo, M. R.; Sardina, F. J. J. Am. Chem. Soc. 2001, 123, 2095-2096.
18. The reverse 5-exo trig addition of the lithium amide onto the dienic system should indeed be favored according to: (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-738; (b) Calaza, M. I.; Paleo, M. R.; Sardina, F. J. J. Am. Chem. Soc. 2001, 123, 2095-2096.
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22. Very convenient procedure: (b) Boeckmann, R. K., Jr.; Shao, P.; Mullins, J. J. Org. Synth. 1999, 77, 141-152.
23. According to the coupling constants: 3b, J=11.2 (Z) and 15.4 (E) Hz/5b, J=11.2 Hz/6, 11.0 (Z) and 15.4 (E) Hz/7, 11.3 Hz. This Z-selectivity on piperidinic substrates seems rather general: (a) Nazabadioko, S.; Perez, R.; J. Brieva, R.; Gotor V. Tetrahedron: Asymmetry 1998, 9, 1597-1604; (b) Sanchez-Sancho, F.; Herradon B. Tetrahedron: Asymmetry 1998, 9, 1951-1965.
24. According to the coupling constants: 3b, J=11.2 (Z) and 15.4 (E) Hz/5b, J=11.2 Hz/6, 11.0 (Z) and 15.4 (E) Hz/7, 11.3 Hz. This Z-selectivity on piperidinic substrates seems rather general: (a) Nazabadioko, S.; Perez, R.; J. Brieva, R.; Gotor V. Tetrahedron: Asymmetry 1998, 9, 1597-1604; (b) Sanchez-Sancho, F.; Herradon B. Tetrahedron: Asymmetry 1998, 9, 1951-1965.
25. Unsubstituted heterocycles have not been considered here since the corresponding lithium amides are probably much less prone to ring fission.
26. Guillam A., Toupet L., Maddaluno J. J. Org. Chem. 63:1998;5110-5122.
27. See about these bases: (a) Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271; (b) Mordini, A. Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol. 1, p. 145; (d) Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446; (e) Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126; (f) Kennedy, A. R.; MacLellan, J. G.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Dalton Trans. 2000, 4112-4116.
28. See about these bases: (a) Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271; (b) Mordini, A. Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol. 1, p. 145; (d) Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446; (e) Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126; (f) Kennedy, A. R.; MacLellan, J. G.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Dalton Trans. 2000, 4112-4116.
29. See about these bases: (a) Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271; (b) Mordini, A. Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol. 1, p. 145; (d) Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446; (e) Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126; (f) Kennedy, A. R.; MacLellan, J. G.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Dalton Trans. 2000, 4112-4116.
30. See about these bases: (a) Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271; (b) Mordini, A. Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol. 1, p. 145; (d) Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446; (e) Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126; (f) Kennedy, A. R.; MacLellan, J. G.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Dalton Trans. 2000, 4112-4116.
31. See about these bases: (a) Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271; (b) Mordini, A. Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol. 1, p. 145; (d) Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446; (e) Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126; (f) Kennedy, A. R.; MacLellan, J. G.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Dalton Trans. 2000, 4112-4116.
32. For a paper taking nice advantage of this phenomenom, see: Watson, P. S.; Jiang, B.; Scott, B. Org. Lett. 2000, 2, 3679-3681.
33. Martin C., Maddaluno J., Duhamel L. Tetrahedron Lett. 37:1996;8169-8172.