Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction

Organic Letters

Volumn 15, Issue 3, 2013, Pages 444-447

  Martin, Rhia M ^a   Bergman, Robert G ^b   Ellman, Jonathan A ^a  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; DIHYDROPYRIDINE DERIVATIVE; LEWIS ACID; QUINUCLIDINE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; CYCLIZATION; CYCLOADDITION REACTION; DIHYDROPYRIDINES; LEWIS ACIDS; MOLECULAR STRUCTURE; QUINUCLIDINES; RHODIUM; STEREOISOMERISM;

EID: 84873387463     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303040r     Document Type: Article

References (76)

1. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337
2. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 2
3. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
4. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
5. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
6. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
9. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
10. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
11. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
12. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
13. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645
14. Duttwyler, S.; Lu, C.; Rheingold, A. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 4064
15. For a recent review on the synthesis of dihydropyridines from pyridines, see: Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642
16. Harrison, D. P.; Sabat, M.; Myers, W. H.; Harman, W. D. J. Am. Chem. Soc. 2010, 132, 17282
17. Harschneck, T.; Kirsch, S. F. J. Org. Chem. 2011, 76, 2145
18. Tejedor, D.; Mendez-Abt, G.; García-Tellado, F. Chem.-Eur. J 2010, 16, 428
19. Padwa, A.; Dean, D. C.; Osterhout, M. H.; Precedo, L.; Semones, M. A. J. Org. Chem. 1994, 59, 5347
20. Martin, R. M.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2012, 77, 2501
21. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 10, 325
22. Too, P. C.; Chua, S. H.; Wong, S. H.; Chiba, S. J. Org. Chem. 2011, 76, 6159
23. Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846
24. MaGee, D. I.; Lee, M. L. Tetrahedron Lett. 2001, 42, 7177
25. Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229
26. MaGee, D. I.; Lee, M. L. Synlett 1997, 7, 786
27. Comins, D. L.; Al-war, R. S. J. Org. Chem. 1992, 57, 4098
28. Baxter, E. W.; Labaree, D.; Chao, S.; Mariano, P. S. J. Org. Chem. 1989, 54, 2893
29. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157
30. Wender, P.; Schaus, J.; Torney, D. Tetrahedron Lett. 1979, 20, 2485
31. Mariano, P. S.; Dunaway-Mariano, D.; Huesmann, P. L. J. Org. Chem. 1979, 44, 124
32. Mariano, P. S.; Dunaway-Mariano, D.; Huesmann, P. L.; Beamer, R. L. Tetrahedron Lett. 1977, 18, 4299
33. Hardin, A. N.; Sarpong, R. Org. Biomol. Chem. 2012, 10, 70
34. Lemonnier, G.; Charette, A. B. J. Org. Chem. 2010, 75, 7465
35. Barbe, G.; St.-Onge, M.; Charette, A. B. Org. Lett. 2008, 10, 5497
36. Maison, W. Eur. J. Org. Chem. 2007, 2276
37. Sales, M.; Charette, A. B. Org. Lett. 2005, 7, 5773
38. Arakawa, Y.; Murakami, T.; Ozawa, F.; Arakawa, Y.; Yoshifuji, S. Tetrahedron 2003, 59, 7555
39. Reding, M. T.; Kaburagi, Y.; Tokuyama, H.; Fukuyama, T. Heterocycles 2002, 56, 313
40. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103
41. Jana, G. K.; Sinha, S. Tetrahedron 2012, 68, 7155
42. Jana, G. K.; Sinha, S. Tetrahedron Lett. 2012, 53, 1671
43. Paul, S.; Pattanayak, S.; Sinha, A. Tetrahedron Lett. 2011, 52, 6166
44. Jana, G. K.; Sinha, S. Tetrahedron Lett. 2010, 51, 1994
45. Hodgson, D. M.; Galano, J.-M. Org. Lett. 2005, 7, 2221
46. Sundberg, R. J.; Cherney, R. J. J. Org. Chem. 1990, 55, 6028
47. Krow, G. R.; Shaw, D. A.; Lynch, B.; Lester, W.; Szczepanski, S. W.; Raghavachari, R.; Derome, A. E. J. Org. Chem. 1988, 53, 2258
48. Sundberg, R. J.; Amat, M.; Fernando, A. M. J. Org. Chem. 1987, 52, 3151
49. Raucher, S.; Bray, B. L. J. Org. Chem. 1985, 50, 3236
50. Raucher, S.; Lawrence, R. F. Tetrahedron Lett. 1983, 24, 2927
51. Sundberg, R. J.; Bloom, J. D. J. Org. Chem. 1981, 46, 4836
52. Marazano, C.; Fourrey, J. L.; Das, B. C. J. Chem. Soc., Chem. Commun. 1981, 37
53. Sundberg, R. J.; Hong, J.; Smith, S. Q.; Sabat, M. Tetrahedron 1998, 54, 6259
54. Comins, D. L.; Bharathi, P.; Sahn, J. J. Tetrahedron Lett. 2012, 53, 1347
55. Oshima, K.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2012, 134, 3699
56. Chou, S.-S.; Wang, H.-C.; Chen, P. W.; Yang, C.-H. Tetrahedron 2008, 64, 5291
57. Songis, O.; Géant, P. Y.; Sautrey, G.; Martinez, J.; Calmès, M. Eur. J. Org. Chem. 2007, 308
58. Hoshino, M.; Matsuzaki, H.; Fujita, R. Heterocycles 2008, 76, 267
59. Krow, G. R.; Huang, Q.; Szczepanski, S. W.; Hausheer, F. H.; Caroll, P. J. J. Org. Chem. 2007, 72, 3458
60. Taylor, S. J.; Taylor, A. M.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 1681
61. Reine, I.; Muceniece, V. L.; Kemme, A. Heterocycl. Commun. 2002, 8, 173
62. dos Santos, D. C.; de Freitas Gil, R. P.; Gil, L.; Marazano, C. Tetrahedron Lett. 2001, 42, 6109
63. Mehmandoust, M.; Marazano, C.; Singh, R.; Gillet, B.; Césario, M.; Fourrey, J.-L.; Das, B. C. Tetrahedron Lett. 1988, 29, 4423
64. Cardellini, M.; Cingolani, G. M.; Claudi, F.; Gulini, U.; Cantalamessa, F.; Venturi, F. Eur. J. Med. Chem. 1987, 22, 1
65. Suttibut, C.; Kohari, Y.; Igarashi, K.; Nakano, H.; Hirama, M.; Seki, C.; Matsuyama, H.; Uwai, K.; Takano, N.; Okuyama, Y.; Osone, K.; Takeshita, M.; Kwon, E. Tetrahedron Lett. 2011, 52, 4745
66. Nakano, H.; Osone, K.; Takeshita, M.; Kwon, E.; Seki, C.; Matsuyama, N.; Kohari, Y. Chem. Commun. 2010, 46, 4827
67. Hirama, M.; Kato, Y.; Maysuyama, H.; Oshikiri, N.; Iyoda, M. Chem. Lett. 2008, 37, 924
68. Nakano, H.; Tsugawa, N.; Takahashi, K.; Okuyama, Y.; Fujita, R. Tetrahedron 2006, 62, 10879
69. Takenaka, N.; Huang.; Rawal, V. H. Tetrahedron 2002, 58, 8299
70. Seki, C.; Hirama, M.; Hutabarat, R.; Takada, J.; Suttibut, C.; Takahashi, H.; Takaguchi, T.; Kohari, Y.; Nakano, H.; Uwai, K.; Takano, N.; Yasui, M.; Okuyama, Y.; Takeshita, M.; Matsuyama, H. Tetrahedron Lett. 2012, 68, 1774
71. Harrison, D. P.; Iovan, D. A.; Myers, W. H.; Sabat, M.; Wang, S.; Zottig, V. E.; Harman, W. D. J. Am. Chem. Soc. 2011, 133, 18378
72. Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 13873
73. Graham, P. M.; Delafuente, D. A.; Lui, W.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 2005, 127, 10568
74. Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685
75. Kimura, H.; Fujiwara, T.; Katoh, T.; Nishide, K.; Node, M. Chem. Pharm. Bull. 2006, 54, 399
76. Nishide, K.; Ichihashi, S.; Kimura, H.; Katoh, T.; Node, M. Tetrahedron Lett. 2001, 42, 9237