Polarization of the pyridine ring: Highly functionalized piperidines from tungsten-pyridine complex

Journal of the American Chemical Society

Volumn 132, Issue 48, 2010, Pages 17282-17295

  Harrison, Daniel P ^a   Sabat, Michal ^a   Myers, William H ^b   Harman, W Dean ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

^b UNIVERSITY OF RICHMOND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPLEXES; DECOMPLEXATIONS; DIHYDROPYRIDINES; FUNCTIONALIZED; PYRIDINE RINGS; STEREOSELECTIVE REACTIONS; SUBSTITUTION PATTERNS;

NUCLEOPHILES; PYRIDINE; TUNGSTEN;

TUNGSTEN COMPOUNDS;

1,2 DIHYDROPYRIDINE COMPLEX; ACID; ALLYL COMPOUND; AMIDE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; TUNGSTEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION; POLARIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 78650081479     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107536w     Document Type: Article

References (37)

1. Davies, S. G. and Shipton, M. R. J. Chem. Soc., Chem. Commun. 1989, 995-996
2. Fish, R. H., Kim, H. S., and Fong, R. H. Organometallics 1989, 8, 1375-1377
3. Wucherer, E. J. and Muetterties, E. L. Organometallics 1987, 6, 1691-1695
4. Meiere, S. H., Brooks, B. C., Gunnoe, T. B., Sabat, M., and Harman, W. D. Organometallics 2001, 20, 1038-1040
5. Cordone, R., Harman, W. D., and Taube, H. J. Am. Chem. Soc. 1989, 111, 2896-2900
6. Cordone, R. and Taube, H. J. Am. Chem. Soc. 1987, 109, 8101-8102
7. Bonanno, J. B., Viege, A. S., Wolczanski, P. T., and Lobkovsky, E. B. Inorg. Chim. Acta 2003, 345, 173-184
8. Kleckley, T. S., Bennett, J. L., Wolczanski, P. T., and Lobkovsky, E. B. J. Am. Chem. Soc. 1997, 119, 247-248
9. Covert, K. J., Neithamer, D. R., Zonnevylle, M. C., LaPointe, R. E., Schaller, C. P., and Wolczanski, P. T. Inorg. Chem. 1991, 30, 2493-2508
10. Neithamer, D. R., Parkanyi, L., Mitchell, J. F., and Wolczanski, P. T. J. Am. Chem. Soc. 1988, 110, 4421-4423
11. Davies, S. G., Edwards, A. J., and Shipton, M. R. J. Chem. Soc., Perkin Trans. 1991, 1009-1017
12. Harrison, D. P., Welch, K. D., Nichols-Nielander, A. C., Sabat, M., Myers, W. H., and Harman, W. D. J. Am. Chem. Soc. 2008, 130, 16844-16845
13. Welch, K. D., Harrison, D. P., Lis, E. C., Liu, W., Salomon, R. J., Harman, W. D., and Myers, W. H. Organometallics 2007, 26, 2791-2794
14. Kosturko, G. W., Harrison, D. P., Sabat, M., Myers, W. H., and Harman, W. D. Organometallics 2009, 28, 387-389
15. The term "dihydropyridine" is a generic description of the 2-substituted 1-acetyl-1,2-dihydropyridine ligands found in Scheme 2.
16. Harrison, D. P., Zottig, V. E., Kosturko, G. W., Welch, K. D., Sabat, M., Myers, W. H., and Harman, W. D. Organometallics 2009, 28, 5682-5690
17. Carbery, D. R. Org. Biomol. Chem. 2008, 6, 3455-3460
18. Lis, E. C., Delafuente, D. A., Lin, Y., Mocella, C. J., Todd, M. A., Liu, W., Sabat, M., Myers, W. H., and Harman, W. D. Organometallics 2006, 25, 5051-5058
19. Liu, W., You, F., Mocella, C. J., and Harman, W. D. J. Am. Chem. Soc. 2006, 128, 1426-1427
20. Schilling, B. E. R., Hoffmann, R., and Faller, J. W. J. Am. Chem. Soc. 1979, 101, 592-598
21. Villanueva, L. A., Ward, Y. D., Lachicotte, R., and Liebeskind, L. S. Organometallics 1996, 15, 4190-4200
22. Tsang, J. Y. K., Buschhaus, M. S. A., Fujita-Takayama, C., Patrick, B. O., and Legzdins, P. Organometallics 2008, 27, 1634-1644
23. Mocella, C. J., Delafuente, D. A., Keane, J. M., Warner, G. R., Friedman, L. A., Sabat, M., and Harman, W. D. Organometallics 2004, 23, 3772-3779
24. Due to the diastereotopic nature of the purported resulting methylene group, deprotonation of such a species likely would also be exo -stereoselective, thus preventing net deuterium incorporation.
25. McEwen, W. E., Calabro, M. A., Mineo, I. C., and Wang, I. C. J. Am. Chem. Soc. 1973, 95, 2392-2393
26. McEwen, W. E. and Cobb, R. L. Chem. Rev. 1955, 55, 511-549
27. Perrin, S., Monnier, K., Laude, B., Kubicki, M., and Blacque, O. Eur. J. Org. Chem. 1999, 297-303
28. Keane, J. M. and Harman, W. D. Organometallics 2005, 24, 1786-1798
29. 2(g) but that its inclusion significantly decreases the required reaction time (from 1 week to <15 h).
30. Molander, G. A. and Jean-Gérard, L. J. Org. Chem. 2009, 74, 5446-5450
31. Schoeps, D., Sashuk, V., Ebert, K., and Plenio, H. Organometallics 2009, 28, 3922-3927
32. Fors, B. P., Krattiger, P., Strieter, E., and Buchwald, S. L. Org. Lett. 2008, 10, 3505-3508
33. Yuan, X., Liu, K., and Li, C. J. Org. Chem. 2008, 73, 6166-6171
34. Taniguchi, T., Yonei, D., Sasaki, M., Tamura, O., and Ishibashi, H. Tetrahedron 2008, 64, 2634-2641
35. Schleich, S. and Helmchen, G. N. Eur. J. Org. Chem. 1999, 2515-2521
36. Evans, D. A., Campos, K. R., Tedrow, J. S., Michael, F. E., and Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905-7920
37. Miller, J. F., Termin, A., Koch, K., and Piscopio, A. D. J. Org. Chem. 1998, 63, 3158-3159