Synthesis of functionalized bicyclic imines via intramolecular azide-alkene 1,3-dipolar cycloaddition/intramolecular stork alkylation cascade reaction

Advanced Synthesis and Catalysis

Volumn 355, Issue 7, 2013, Pages 1237-1242

  De Miguel, Irene ^a   Velado, Marina ^a   Herradón, Bernardo ^a   Mann, Enrique ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

azides; cycloaddition; piperideines; pyrrolines; Stork alkylation

Indexed keywords

EID: 84877687019     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201201027     Document Type: Article

References (62)

1. A. Otero, M. J. Chapela, M. Atanassova, J. M. Vieites, A. G. Cabado, Chem. Res. Toxicol. 2011, 24, 1817-1829.
2. Y. Zhang, L. Pan, X. Xu, Q. Liu, RSC Adv. 2012, 2, 5138-5140
3. B. C. J. van Esseveldt, P. W. H. Vervoort, F. L. van Delft, F. P. J, T. Rutjes, J. Org. Chem. 2005, 70, 1791-1795
4. T. Kondo, T. Okada, T. Mitsudo, J. Am. Chem. Soc. 2002, 124, 186-187
5. B. G. Davis, M. A. T. Maughan, T. M. Chapman, R. Villard, S. Courtney, Org. Lett. 2002, 4, 103-106
6. S. Takayama, R. Martin, J. Wu, K. Laslo, G. Siuzdak, C. H. Wong, J. Am. Chem. Soc. 1997, 119, 8146-8151
7. N. G. De Kimpe, M. A. Keppens, C. V. Stevens, Tetrahedron Lett. 1993, 34, 4693-4696
8. J. Boivin, E. Fouquet, S. Z. Zard, Tetrahedron Lett. 1990, 31, 85-88
9. T. Saegusa, Y. Ito, H. Kinoshita, S. Tomita, J. Org. Chem. 1971, 36, 3316-3323.
10. V. V. R. Kondakal, M. I. Qamar, K. Hemming, Tetrahedron Lett. 2012, 53, 4100-4103
11. B. Lee, J. Kwon, C.-M. Yu, Synlett 2009, 1498-1500.
12. N. Fleury-Brégeot, V. de La Fuente, S. Castillón, C. Claver, ChemCatChem 2010, 2, 1346-1371
13. K. Gao, B. Wu, C.-B. Yu, Q.-A. Chen, Z.-S. Ye, Y.-G. Zhou, Org. Lett. 2012, 14, 3890-3893
14. M. Chang, W. Li, X. Zhang, Angew. Chem. 2011, 123, 10867-10869
15. Angew. Chem. Int. Ed. 2011, 50, 10679-10681
16. G.-H. Hou, J.-H. Xie, P.-C. Yan, Q-L. Zhou, J. Am. Chem. Soc. 2009, 131, 1366-1367.
17. M. Rueping, E. Merino, R. M. Koenigs, Adv. Synth. Catal. 2010, 352, 2629-2634
18. N. Haraguchi, K. Tsuru, Y. Arakawa, S. Itsuno, Org. Biomol. Chem. 2009, 7, 69-75
19. J. Wu, F. Wang, Y. Ma, X. Cui, L. Cun, J. Zhu, J. Deng, B. Yu, Chem. Commun. 2006, 1766-1768.
20. S. M.-C. Pelletier, P. C. Ray, D. J. Dixon, Org. Lett. 2009, 11, 4512-4515
21. Y. Tang, J. C. Fettinger, J. T. Shaw, Org. Lett. 2009, 11, 3802-3805
22. P. Jakubec, M. Hellwell, D. J. Dixon, Org. Lett. 2008, 10, 4267-4270.
23. Y. Luo, A. J. Carnell, H. W. Lam, Angew. Chem. Int. Ed. 2012, 51, 6762 -6766
24. N. E. Shevchenko, V. G. Nenajdenko, G.-V. Röschenthaler, J. Fluorine Chem. 2008, 129, 390-396
25. T. M. Chapman, S. Courtney, P. Hay, B. G. Davis, Chem. Eur. J. 2003, 9, 3397-3414.
26. M. Dhooghe, K. A. Tehrani, N. De Kimpe, Tetrahedron 2009, 65, 3753-3756
27. K. A. Tehrani, M. Dhooghe, N. De Kimpe, Tetrahedron 2003, 59, 3099-3108
28. D. A. Evans, J. Am. Chem. Soc. 1970, 92, 7593-7595.
29. F. Sánchez-Sancho, E. Mann, B. Herradón, Adv. Synth. Catal. 2001, 343, 360-368
30. F. Sánchez-Sancho, E. Mann, B. Herradón, Synlett 2000, 509-513
31. F. Sánchez-Sancho, B. Herradón, Tetrahedron: Asymmetry 1998, 9, 1951-1965.
32. I. de Miguel, B. Herradón, E. Mann, Adv. Synth. Catal. 2012, 354, 1731-1736.
33. L. Wolff, Justus Liebigs Ann. Chem. 1912, 394, 23-59
34. R. Huisgen, Angew. Chem. 1963, 75, 604-637
35. Angew. Chem. Int. Ed. Engl. 1963, 2, 565-632.
36. A. L. Logothetis, J. Am. Chem. Soc. 1965, 87, 749-754.
37. I. de Miguel, M. Velado, B. Herradón, E. Mann, Eur. J. Org. Chem. 2012, 4347-4353
38. B. W. Q. Hui, S. Chiba, Org. Lett. 2009, 11, 729-732
39. Y. Zhou, P. V. Murphy, Org. Lett. 2008, 10, 3777-3780
40. S. Kim, Y. M. Lee, J. Lee, T. Lee, Y. Fu, Y. Song, J. Cho, D. Kim, J. Org. Chem. 2007, 72, 4886-4891
41. Y. Konda-Yamada, K. Asano, T. Satou, S. Monma, M. Sakayanagi, N. Satou, K. Takeda, Y. Harigaya, Chem. Pharm. Bull. 2005, 53, 529-536
42. V. Santagada, E. Perissutti, F. Fiorino, B. Vivenzio, G. Caliendo, Tetrahedron Lett. 2001, 42, 2397-2400
43. W. H. Pearson, H. Suga, J. Org. Chem. 1998, 63, 9910-9918
44. J. M. Schkeryantz, W. H. Pearson, Tetrahedron 1996, 52, 3107-3116
45. D. F. Taber, P. B. Deker, L. J. Silverberg, J. Org. Chem. 1992, 57, 5990-5994
46. R. B. Bennet, J. R. Choi, W. D. Montgomery, J. K. Cha, J. Am. Chem. Soc. 1989, 111, 2580-2582.
47. Y. Hayashi, H. Gotoh, T. Tamura, H. Yamaguchi, R. Masui, M. Shoji, J. Am. Chem. Soc. 2005, 127, 16028-16029
48. M. T. Hechavarria, B. List, Angew. Chem. 2004, 116, 4048-4050
49. Angew. Chem. Int. Ed. 2004, 43, 3958-3960
50. G. U. Gunawardena, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1997, 119, 2066-2067
51. F. Dumas, J. dAngelo, Tetrahedron: Asymmetry 1990, 1, 167-170
52. D. Seebach, M. Missbach, G. Calderari, M. Eberle, J. Am. Chem. Soc. 1990, 112, 7625-7638
53. J. dAngelo, C. Ferroud, Tetrahedron Lett. 1989, 30, 6511-6514
54. S. L. Schreiber, H. V. Meyers, J. Am. Chem. Soc. 1988, 110, 5198-5200.
55. G. Stork, H. K. Landesman, J. Am. Chem. Soc. 1956, 78, 5128-5129
56. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, R. Terrell, J. Am. Chem. Soc. 1963, 85, 207-222.
57. M. Movassaghi, B. Chen, Angew. Chem. 2007, 119, 571-574
58. Angew. Chem. Int. Ed. 2007, 46, 565-568
59. M. J. Lee, K. Y. Lee, D. Y. Park, J. N. Kim, Bull. Korean Chem. Soc. 2005, 26, 1281-1285.
60. T. Janecki, J. Kedzia, T. Wasek, Synthesis 2009, 1227-1254.
61. N. De Kimpe, M. Keppens, Tetrahedron 1996, 52, 3705-3718
62. L. A. Cohen, B. Witkop, J. Am. Chem. Soc. 1955, 77, 6595-6600.