Synthesis and resolution of a chiral analogue of 2,2,6,6- tetramethylpiperidine and of its corresponding nitroxide

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2565-2568

  Einhorn, Jacques ^a   Einhorn, Cathy ^a   Ratajczak, Fabien ^a   Durif, André ^a   Averbuch, Marie Thérèse ^a   Pierre, Jean Louis ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NITROXIDE; TEMPOL; TEMPONE;

ARTICLE; CONFORMATIONAL TRANSITION; ENANTIOMER; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032560087     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00244-5     Document Type: Article

References (26)

1. 2 symmetric amines in synthesis see references cited therein.
2. 2. See for example: Misumi, A.; Iwagana, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343-3345; Dougherty, C. M.; Olofson, R.A. Org. Synth. Coll. Vol. 6 1988, 571-575 and references cited therein; Yanagisawa, A.; Yasur, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun., 1994, 2103-2104; Schlecker, W.; Huth, A.; Ottow, E. J. Org. Chem., 1995, 60, 8414-8416.
3. 2. See for example: Misumi, A.; Iwagana, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343-3345; Dougherty, C. M.; Olofson, R.A. Org. Synth. Coll. Vol. 6 1988, 571-575 and references cited therein; Yanagisawa, A.; Yasur, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun., 1994, 2103-2104; Schlecker, W.; Huth, A.; Ottow, E. J. Org. Chem., 1995, 60, 8414-8416.
4. 2. See for example: Misumi, A.; Iwagana, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343-3345; Dougherty, C. M.; Olofson, R.A. Org. Synth. Coll. Vol. 6 1988, 571-575 and references cited therein; Yanagisawa, A.; Yasur, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun., 1994, 2103-2104; Schlecker, W.; Huth, A.; Ottow, E. J. Org. Chem., 1995, 60, 8414-8416.
5. 2. See for example: Misumi, A.; Iwagana, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343-3345; Dougherty, C. M.; Olofson, R.A. Org. Synth. Coll. Vol. 6 1988, 571-575 and references cited therein; Yanagisawa, A.; Yasur, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun., 1994, 2103-2104; Schlecker, W.; Huth, A.; Ottow, E. J. Org. Chem., 1995, 60, 8414-8416.
6. 3. Ma, Z.; Huang, Q.; Bobbitt, J.M. J. Org. Chem. 1993, 58, 4837-4843; Rychnovsky, S.D.; Mc Lernon, T.L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194-1195.
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8. 4. Tamura, R.; Susuki, S.; Azuma, N.; Matsumoto, A.; Toda. F.; Kamimura, A.; Hori, K. Angew. Chem. Int. Ed. Engl. 1994, 33, 878-879; Tamura, R.; Susuki, S.; Azuma, N.; Matsumoto, A.; Toda, F.; Ishii, Y. J. Org. Chem. 1995, 60, 6820-6825.
9. 4. Tamura, R.; Susuki, S.; Azuma, N.; Matsumoto, A.; Toda. F.; Kamimura, A.; Hori, K. Angew. Chem. Int. Ed. Engl. 1994, 33, 878-879; Tamura, R.; Susuki, S.; Azuma, N.; Matsumoto, A.; Toda, F.; Ishii, Y. J. Org. Chem. 1995, 60, 6820-6825.
10. 5. Braslau, R.; Burrill II, L.C.; Mahal, L.K.; Wedeking, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 237-238.
11. 6. Puts, R.D.; Sogah, D.Y. Macromolecules 1996, 29, 3323-3325.
12. 7 For a general review on the synthesis and applications of optically active nitroxides, see: Naik, N.; Braslau, R. Tetrahedron 1998, 54, 667-696.
13. 8. Lee, T.D.; Birrel, G.B.; Keana, J.F.W. J. Am. Chem. Soc. 1978, 100, 1618-1619; Keana, J.F.W.; Seyedrezai, S.E.; Gaughan, J. J. Org. Chem. 1983, 48, 2644-2647; Keana, J. F. W.; Cuomo, J.; Lex, L.; Seyedrezai, S.E. J. Org. Chem.. 1983, 48, 2647-2654; Keana, J.F.W.; Prabhu, V.S. J. Org. Chem. 1986, 51, 4300-4301.
14. 8. Lee, T.D.; Birrel, G.B.; Keana, J.F.W. J. Am. Chem. Soc. 1978, 100, 1618-1619; Keana, J.F.W.; Seyedrezai, S.E.; Gaughan, J. J. Org. Chem. 1983, 48, 2644-2647; Keana, J. F. W.; Cuomo, J.; Lex, L.; Seyedrezai, S.E. J. Org. Chem.. 1983, 48, 2647-2654; Keana, J.F.W.; Prabhu, V.S. J. Org. Chem. 1986, 51, 4300-4301.
15. 8. Lee, T.D.; Birrel, G.B.; Keana, J.F.W. J. Am. Chem. Soc. 1978, 100, 1618-1619; Keana, J.F.W.; Seyedrezai, S.E.; Gaughan, J. J. Org. Chem. 1983, 48, 2644-2647; Keana, J. F. W.; Cuomo, J.; Lex, L.; Seyedrezai, S.E. J. Org. Chem.. 1983, 48, 2647-2654; Keana, J.F.W.; Prabhu, V.S. J. Org. Chem. 1986, 51, 4300-4301.
16. 8. Lee, T.D.; Birrel, G.B.; Keana, J.F.W. J. Am. Chem. Soc. 1978, 100, 1618-1619; Keana, J.F.W.; Seyedrezai, S.E.; Gaughan, J. J. Org. Chem. 1983, 48, 2644-2647; Keana, J. F. W.; Cuomo, J.; Lex, L.; Seyedrezai, S.E. J. Org. Chem.. 1983, 48, 2647-2654; Keana, J.F.W.; Prabhu, V.S. J. Org. Chem. 1986, 51, 4300-4301.
17. 9. Benfaremo, N.; Steenbock, M.; Klapper, M.; Müllen, K.; Enkelmann, V; Cabrera, K. Liebigs Ann; 1996, 1413-1415.
18. 10. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Gautier-Luneau, J; Pierre, J.L. J. Org. Chem. (in press).
19. 11. Goti, A.; Nanelli, L. Tetrahedron Lett. 1996, 37, 6025-6028.
20. 22NO : C, 81.39; H, 7.91; N, 5.00. Found: C, 81.59; H, 7.83; N, 5.04.
21. w = 0.038, for 1306 reflections with I > 3σ(I) and 191 variables. Data were recorded on a Nonius CAD4 diffractometer with Mo-Kα radiation. The structure was solved by direct methods (Sir 92) and refined using full-matrix least squares methods. Hydrogen atoms were included, but not refined. Full data will be deposited at the Cambridge Crystallographic Data Center (CCDC). For a comparison with the X-ray data of the homologous pyrrolidinyl nitroxide, see ref. 9.
22. 14. Rosantsev, E.G.; Sholle, V.D. Synthesis 1971, 401-414.
23. 3 + isobutane) : m/z (%) = 266 (100), 250 (19.5).
24. 16. Brik, M.E. Tetrahedron Lett. 1995, 36, 5519-5520.
25. -1.
26. 18. Attemps to determine the enantiomeric purity of amine 5 directly by chiral HPLC or by using NMR techniques have failed so far.