Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines

Journal of the American Chemical Society

Volumn 125, Issue 21, 2003, Pages 6360-6361

  Legault, Claude ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

N BENZOYLIMINOPYRIDINIUMYLIDE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL MODIFICATION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

CRYSTALLOGRAPHY, X-RAY; PIPERIDINES; PYRIDINIUM COMPOUNDS;

EID: 0038514200     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0348647     Document Type: Article

References (34)

1. (a) Laschat, S.; Dickner, T. Synthesis 2000, 1781-1813.
2. (b) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892.
3. Indolizidine/quinolizidine: Michael, J. P. Nat. Prod. Rep. 2001, 18, 520-542.
4. (a) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651-2652.
5. (b) Comins, D. L.; Zhang, Y. J. Am. Chem. Soc. 1996, 118, 12248-12249.
6. (c) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807-3811.
7. (d) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719-4728.
8. (a) Guilloteau-Bertin, B.; Compère, D.; Gil, L.; Marazano, C.; Das, B. C. Eur. J. Org. Chem. 2000, 1391-1399.
9. (b) Génisson, Y.; Marazano, C.; Das, B. C. J. Org. Chem. 1993, 58, 2052-2057.
10. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830.
11. (a) Schiess, P.; Monnier, C.; Ringele, P.; Sendi, E. Helv. Chim. Acta 1974, 57, 1676-1691.
12. (b) Van Bergen, T. J.; Kellogg, R. M. J. Org. Chem. 1971, 36, 1705-1708.
13. (a) Tamura, Y.; Ikeda, M. Adv. Heterocycl. Chem. 1981, 29, 71-137.
14. (b) Timpe, H. J. Adv. Heterocycl. Chem. 1974, 17, 213-253.
15. (a) Yeung, J. M.; Corleto, L. A.; Knaus, E. E. J. Med. Chem. 1982, 25, 191-195.
16. (b) Yeung, J. M.; Corleto, L. A.; Knaus, E. E. J. Med. Chem. 1982, 25, 720-723.
17. (c) Knaus, E. E.; Redda, K. J. Heterocycl. Chem. 1976, 13, 1237-1240.
18. N-Aminopyridinium iodide is commercially available through Lancaster.
19. Gösl, R.; Meuwsen, A. Org. Synth. 1963, 43, 1.
20. Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1-17.
21. NAPBz is a white nonhygroscopic crystalline solid which can be kept for months on the workbench without any noticeable decomposition.
22. For an extended structural analysis of 1, see Supporting Information.
23. Holm, T. Acta Chem. Scand. 1991, 45, 276-279.
24. (a) Brana, M. F.; Morán, M.; Pérez de Vega, M. J.; Pita-Romero, I. J. Org. Chem. 1996, 61, 1369-1374.
25. (b) Brana, M. F.; Morán, M.; Pérez de Vega, M. J.; Pita-Romero, I. Tetrahedron Lett. 1994, 35, 8655-8658.
26. (c) Krow, G. R.; Lee, Y. B.; Raghavachari, R.; Szczepanski, S. W. Tetrahedron 1991, 47, 8499-8514.
27. (d) Yamaguchi, R.; Moriyasu, M.; Yoshioka, M.; Kawanisi, M. J. Org. Chem. 1988, 53, 3507-3512.
28. (e) Yamaguchi, R.; Hata, E.; Matsuki, T.; Kawanisi, M. J. Org. Chem. 1987, 52, 2094-2096.
29. (f) Yamaguchi, R.; Nakazono, Y.; Matsuki, T.; Hata, E.; Kawanisi, M. Bull. Chem. Soc. Jpn. 1987, 60, 215-222.
30. (g) Krow, G. R.; Cannon, K. C.; Carey, J. T.; Lee, Y. B.; Szczepanski, S. W. J. Heterocycl. Chem. 1985, 22, 131-135.
31. (h) Yamaguchi, R.; Moriyasu, M.; Yoshioka, M.; Kawanisi, M. J. Org. Chem. 1985, 50, 287-288.
32. (i) Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1984, 25, 3297-3300.
33. 2O afforded (±)-cis-2-methyl-6-propylpiperidine hydrochloride 11 (91%).
34. Denmark, S. E.; Nicaise, O.; Edwards, J. P. J. Org. Chem. 1990, 55, 6219-6223. By applying these conditions to 2g followed by in situ trapping with benzyl chloroformate, we isolated the corresponding CBz protected tetrahydropyridine in 87% yield.