Preparation of trans- and cis-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines based on the reductive trans-2,6-dialkylation of pyridine. Synthesis of (±)-epidihydropinidine and (±)-dihydropinidine

Russian Chemical Bulletin

Volumn 47, Issue 3, 1998, Pages 451-458

  Bubnov, Yu N ^a   Klimkina, E V ^a   Ignatenko, A V ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

( ) dihydropin; ( ) epidihydropinidine; Allylboration; Piperidine alkaloids; Pyridine, 1,2 addition, alkyl(aryl)lithium, triallylborane; Stereochemistry; Trans and cis 2 allyl 6 alkyl(aryl) 1,2,3,6 tetrahydropyridines; Trans cis isomerization

Indexed keywords

EID: 0000917161     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02495652     Document Type: Article

References (43)

1. a) M. T. Schneider, J. A. Montali, and C. E. Stanton, J. Nat. Prod., 1991, 54, 905;
2. b) J. N. Tawara, A. Blokhin, T. A. Federraro, F. R. Stermitz, and H. Hope, J. Org. Chem., 1993, 58, 4813 and references therein;
3. c) F. R. Stermitz, J. N. Tawara, M. Boeckl, M. Pomeroy, T. A. Federraro, and F. G. Todd, Phytochemistry, 1994, 35, 951;
4. d) J. N. Tawara, F. R. Stermitz, and A. V. Blokhin, Phytochemistry, 1995, 39, 705;
5. e) F. G. Todd, F. R. Stermitz, and A. V. Blokhin, Phytochemistry, 1995, 40 (2), 401.
6. W. V. Brown and B. P. Moore, Aust. J. Chem., 1982, 35, 1255.
7. A. B. Attygalle, S.-C. Xu, K. D. McCormick, J. Meinwald, C. L. Blankespoor, and T. Eisner, Tetrahedron, 1993, 49, 9333.
8. Alkaloids: Chemical and Biological Perspectives, Ed. S. W. Pelletier, Wiley, New York, 1985, vol. 3, 1986, vol. 4.
9. Alkaloids: Chemical and Biological Perspectives, Ed. S. W. Pelletier, Wiley, New York, 1985, vol. 3, 1986, vol. 4.
10. S. Leclercq, I. Thirionet, F. Broeders, D. Daloze, R. V. Meer, and J. C. Braekman, Tetrahedron, 1994, 50 (28), 8465.
11. a) D. M. Ryckman and R. V. Stevens, J. Org. Chem., 1987, 52, 4274 and references therein;
12. b) D. L. Comins, and M. A. Weglarz, J. Org. Chem., 1991, 56, 2506;
13. c) T.-K. Yang, T.-F. Teng, J.-H. Lin, and Y.-Y. Lay, Tetrahedron Lett., 1994, 35, 3581 and references therein;
14. d) D. L. Comins, G. Chung, and M. A. Foley, Heterocycles, 1994, 37, 1121.
15. a) H. Takahata, H. Bandoh, M. Hanayama, and T. Momose, Tetrahedron: Asymmetry, 1992, 3, 607;
16. b) N. Yamazaki, and C. Kibayashi, J. Am. Chem. Soc., 1989, 111, 1396;
17. c) R. E. Dolle, K. I. Osifo, and C.-S. Li, Tetrahedron Lett., 1991, 32, 5029;
18. d) Z. H. Lu and W.-S. Zhou, J. Chem. Soc., Perkin Trans. 1, 1993, 593.
19. a) R. Chenevert and M. Dickman, J. Org. Chem., 1996, 61, 3332 and references therein;
20. b) W. Oppolzer, C. G. Bocher, and E. Merifield, Tetrahedron Lett., 1994, 35 (38), 7015;
21. c) G. Solladi and N. Huser, Recl. Trav. Chim. Pays-Bass, 1995, 114 (4/5), 153.
22. Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, A. V. Ignatenko, and I. D. Gridnev, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2644 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 2315 (Engl. Transl.)].
23. Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, A. V. Ignatenko, and I. D. Gridnev, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2644 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 2315 (Engl. Transl.)].
24. a) Yu. N. Bubnov, Pure Appl. Chem., 1994, 66, 235;
25. b) Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1994, 693 [Russ. Chem. Bull., 1994, 43, 645 (Engl. Transl.)];
26. b) Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1994, 693 [Russ. Chem. Bull., 1994, 43, 645 (Engl. Transl.)];
27. c) Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, M. O. Dekaprilevich, and Yu. T. Struchkov, Izv. Akad. Nauk, Ser. Khim., 1994, 705 [Russ. Chem. Bull., 1994, 43, 657 (Engl. Transl.)].
28. c) Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, M. O. Dekaprilevich, and Yu. T. Struchkov, Izv. Akad. Nauk, Ser. Khim., 1994, 705 [Russ. Chem. Bull., 1994, 43, 657 (Engl. Transl.)].
29. a) Yu. N. Bubnov, E. E. Demina, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1997, 627 [Russ. Chem. Bull., 1997, 46, 606 (Engl. Transl.)];
30. a) Yu. N. Bubnov, E. E. Demina, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1997, 627 [Russ. Chem. Bull., 1997, 46, 606 (Engl. Transl.)];
31. b) Yu. N. Bubnov, E. E. Demina, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1997, 1361 [Russ. Chem. Bull., 1997, 46, 1306 (Engl. Transl.)]
32. b) Yu. N. Bubnov, E. E. Demina, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1997, 1361 [Russ. Chem. Bull., 1997, 46, 1306 (Engl. Transl.)]
33. S. V. Evchenko, Ph.D. (Chem.) Thesis, Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 1994 (in Russian)
34. a) K. Ziegler and H. Zeiser, Ber., 1930, 63, 1847;
35. b) E. F. V. Scriven, in: Comprehensive Heterocyclic Chemistry; A. R. Katritzky and W. Rees, eds., Pergamon Press: Oxford, 1984; Vol. 2, Part 2 A, pp. 262-266.
36. a) Yu. N. Bubnov, E. V. Klimkina, A. V. Ignatenko, and I. D. Gridnev, Tetrahedron Lett., 1996, 37, 1337;
37. b) Yu. N. Bubnov, E. V. Klimkina, A. V. Ignatenko, and I. D. Gridnev, Tetrahedron Lett., 1997, 38, 4631.
38. W. Clegg, L. Dunbar, L. Horsburgh, and R. E. Milvey, Angew. Chem. Int. Ed. Engl., 1996, 35, 753.
39. F. Haglid, Acta Chem. Scand., 1967, 21, 335.
40. R. F. Frencis, W. Davis, and J. T. Wischer, J. Org. Chem., 1974, 39, 59.
41. Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions; Palm, V. A. Ed.; VINITI: Moscow, 1974; vol. II(1), pp. 200 and 223.
42. Yu. N. Bubnov, E. V. Klimkina, M. O. Dekaprilevich, and Yu. T. Struchkov, Izv. Akad. Nauk, Ser. Khim., 1996, 2736 [Russ. Chem. Bull., 1996, 45, 2595 (Engl. Transl.)].
43. Yu. N. Bubnov, E. V. Klimkina, M. O. Dekaprilevich, and Yu. T. Struchkov, Izv. Akad. Nauk, Ser. Khim., 1996, 2736 [Russ. Chem. Bull., 1996, 45, 2595 (Engl. Transl.)].