Efficient synthesis of α,β-unsaturated alkylimines performed with allyl cations and azides: Application to the synthesis of an ant venom alkaloid

Organic Letters

Volumn 14, Issue 22, 2012, Pages 5728-5731

  Hayashi, Kyohei ^a   Tanimoto, Hiroki ^a   Zhang, Huan ^a   Morimoto, Tsumoru ^a   Nishiyama, Yasuhiro ^a   Kakiuchi, Kiyomi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANT VENOM; AZIDE; IMINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COSTA RICA; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; ANT VENOMS; AZIDES; CATALYSIS; COSTA RICA; IMINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84869191677     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302608q     Document Type: Article

References (46)

1. Tanaka, K.; Siwu, E. R. O.; Hirosaki, S.; Iwata, T.; Matsumoto, R.; Kitagawa, Y.; Pradipta, A. R.; Okumura, M.; Fukase, K. Tetrahedron Lett. 2012, 53, 5899-5902
2. Hachiya, I.; Mizota, M.; Shimizu, M. Heterocycles 2012, 85, 993-1016
3. Duttwyler, S.; Lu, C.; Rheingold, A. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 4064-4067
4. Oberg, K. M.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 4785-4787
5. Marcoux, D.; Bindschädler, P.; Speed, A. W. H.; Chiu, A.; Pero, J. E.; Borg, G. A.; Evans, D. A. Org. Lett. 2011, 13, 3758-3761
6. Johannes, J. W.; Wenglowsky, S.; Kishi, Y. Org. Lett. 2005, 7, 3997-4000
7. Hong, B.-C.; Wu, J.-L.; Gupta, A. K.; Hallur, M. S.; Liao, J.-H. Org. Lett. 2004, 6, 3453-3456
8. Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099-6138
9. Fletcher, M. D.; Hurst, T. H.; Miles, T. J.; Moody, C. J. Tetrahedron 2006, 62, 5454-5463
10. Kobayashi, S.; Furuya, T.; Otani, T.; Saito, T. Tetrahedron 2008, 64, 9705-9716
11. Chen, W.-S.; Fowder, F. W.; Lupo, A. T., Jr. J. Am.Chem. Soc. 1981, 103, 2090-2091
12. François, D.; Maden, A.; Murray, W. V. Org. Lett. 2004, 6, 1931-1934
13. Gagnon, D.; Spino, C. J. Org. Chem. 2009, 74, 6035-6041
14. Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713-1729
15. Schuster, E.; Hesse, C.; Schumann, D. Synlett 1991, 916-918 and references therein
16. Bräse, S.; Banert, K. Organic Azides, Syntheses and Applications; John Wiley & Sons: Ltd.: Chichester, 2010.
17. Wrobleski, A.; Coombs, T. C.; Huh, C. W.; Li, S.-W.; Aubé, J. Org. React. 2012, 78, 1-320
18. Chiba, S. Synlett 2012, 23, 21-44
19. Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247-12275
20. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240
21. Banerjee, A.; Kumar, P. S.; Baskaran, S. Chem. Commun. 2011, 47, 12218-12220
22. Pearson, W. H.; Fang, W. K. J. Org. Chem. 2000, 65, 7158-7174
23. Molina, P.; Alcántara, J.; Leonardo, L. Synlett 1995, 363-364
24. Pearson, W. H.; Fang, W. K. J. Org. Chem. 1995, 60, 4960-4961
25. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickendorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194
26. Scadeng, O.; Ferguson, M. J.; West, F. G. Org. Lett. 2011, 13, 114-117
27. Grecian, S.; Desai, P.; Mossman, C.; Poutsma, J. L.; Aubé, J. J. Org. Chem. 2007, 72, 9439-9447
28. Pearson, W. H.; Fang, W. K.; Kampf, J. W. J. Org. Chem. 1994, 59, 2682-2684
29. Kapat, A.; Nyfeler, E.; Giuffredi, G. T.; Renaud, P. J. Am. Chem. Soc. 2009, 131, 17746-17747
30. de Miguel, E.; Valedo, M.; Herradón, B.; Mann, E. Eur. J. Org. Chem. 2012, 4347-4353
31. Zhao, Y.-M.; Gu, P.; Tu, Y.-Q.; Zhang, H.-J.; Zhang, Q.-W.; Fan, C.-A. J. Org. Chem. 2010, 75, 5289-5295
32. Zhou, Y.; Murphy, P. V. Org. Lett. 2008, 10, 3777-3780
33. Kim, S.; Lee, Y. M.; Lee, T.; Fu, Y.; Song, Y.; Cho, J.; Kim, D. J. Org. Chem. 2007, 72, 4886-4891
34. Schkeryantz, J.; Pearson, W. H. Tetrahedron 1996, 52, 3107-3116
35. Hudlicky, T.; Luna, J. H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687
36. Reddy, D. S.; Judd, W. R.; Aubé, J. Org. Lett. 2003, 5, 3899-3902
37. Kozikowski, A.; Greco, M. N. J. Org. Chem. 1984, 49, 2310-2314
38. Chida, N. Keio University, personal communication, 2008. Recently, Feldman et al. have developed allenyl azide cycloaddition chemistry which produces bicyclic unsaturated imines. See
39. Feldman, K. S.; Antoline, J. F. Org. Lett. 2012, 14, 934-937
40. Feldman, K. S.; Iyer, M. R. J. Am. Chem. Soc. 2006, 127, 4590-4591
41. Eckert, F.; Leito, I.; Kaljurand, I.; Kütt, A.; Klamt, A.; Diedenhofen, M. J. Comput. Chem. 2009, 30, 799-810
42. Barbero, M.; Cadamuro, S.; Dughera, S.; Venturello, P. Synthesis 2008, 1379-1388
43. Jia, A. K.; Ottosson, H.; Zen, X.; Thibblin, A. J. Org. Chem. 2002, 67, 182-187
44. Goering, H. L.; Dilgren, R. E. J. Am. Chem. Soc. 1959, 81, 2556-2561
45. The reaction with trans -cinnamyl alcohol gave 14b in 20% yield without ketones or ketimines.
46. Jones, T. H.; DeVries, P. J.; Escoubas, P. J. Chem. Ecol. 1991, 17, 2507-2518. The absolute stereochemistry or optical rotation value was not provided in this paper