Synthesis of azacycles based on iridium-catalyzed sequential allylic amination

Synlett

Volumn , Issue 7, 2003, Pages 1031-1033

  Miyabe, Hideto ^a   Yoshida, Kazumasa ^a   Kobayashi, Yusuke ^a   Matsumura, Akira ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Amination; Azacycles; Cyclizations; Iridium

Indexed keywords

ALLYL COMPOUND; CARBONIC ACID; IRIDIUM;

AMINATION; ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0038575883     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39317     Document Type: Article

References (28)

1. Pearson, W. H. Studies in Natural Product Chemistry, Vol. 1; Atta-Ur-Rahman, Ed.; Elsevier: Amsterdam, 1988, 323-358.
2. (a) For a recent review, see: Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493.
3. (b) For some recent examples, see: Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469.
4. (c) Verma, S. K.; Atanes, M. N.; Busto, J. B.; Thai, D. L.; Rapoport, H. J. Org. Chem. 2002, 67, 1314.
5. (d) See also: Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982.
6. (e) Chakraborty, T. K.; Srinivasu, P.; Kumar, S. K.; Kunwar, A. C. J. Org. Chem. 2002, 67, 2093.
7. (f) Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
8. (g) See further: Hsu, R.; Cheng, L.; Chang, N.; Tai, H. J. Org. Chem. 2002, 67, 5044.
9. (h) Neipp, C. E.; Martin, S. F. Tetrahedron Lett. 2002, 43, 1779.
10. (i) Aggarwal, V. K.; Sandrinelli, F.; Charmant, J. P. H. Tetrahedron: Asymmetry 2002, 13, 87.
11. (j) Comins, D. L.; Zheng, X.; Goehring, R. R. Org. Lett. 2000, 2, 1611.
12. (k) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503.
13. (l) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929.
14. For a recent review on allylic amination, see: Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689.
15. For some examples, see: (a) Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguch, S. J. Org. Chem. 1997, 62, 776. (b) Yokoyama, H.; Otaya, K.; Kobayashi, H.; Miyazawa, M.; Yamaguch, S.; Hirai, Y. Org. Lett. 2000, 2, 2427. (c) Ma, S.; Gao, W. Org. Lett. 2002, 4, 2989.
16. For some examples, see: (a) Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguch, S. J. Org. Chem. 1997, 62, 776. (b) Yokoyama, H.; Otaya, K.; Kobayashi, H.; Miyazawa, M.; Yamaguch, S.; Hirai, Y. Org. Lett. 2000, 2, 2427. (c) Ma, S.; Gao, W. Org. Lett. 2002, 4, 2989.
17. For some examples, see: (a) Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguch, S. J. Org. Chem. 1997, 62, 776. (b) Yokoyama, H.; Otaya, K.; Kobayashi, H.; Miyazawa, M.; Yamaguch, S.; Hirai, Y. Org. Lett. 2000, 2, 2427. (c) Ma, S.; Gao, W. Org. Lett. 2002, 4, 2989.
18. Palladium-catalyzed tandem allylation of diamines was recently reported, see: Yang, S.-C.; Shue, Y.-J.; Liu, P.-C. Organometallics 2002, 21, 2013.
19. The iridium-catalyzed regioselective allylic amination was studied by Takeuchi's group. See: (a) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 1, 265. (c) Takeuchi, R. Synlett 2002, 1954.
20. The iridium-catalyzed regioselective allylic amination was studied by Takeuchi's group. See: (a) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 1, 265. (c) Takeuchi, R. Synlett 2002, 1954.
21. The iridium-catalyzed regioselective allylic amination was studied by Takeuchi's group. See: (a) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525. (b) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 1, 265. (c) Takeuchi, R. Synlett 2002, 1954.
22. Our studies on the iridium-catalyzed reaction. See: (a) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem. Int. Ed. 2003, in press. (b) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
23. Our studies on the iridium-catalyzed reaction. See: (a) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem. Int. Ed. 2003, in press. (b) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
24. 4, and concentrated at reduced pressure. Purification of the residue by flash chromatography (hexane:EtOAc = 10:1) afforded 4a or 5-7.
25. 1H NMR data showed similarity with the related 2,6-disubstituted piperidines. In general, the signals due to the N-benzylic hydrogen of cis-2,6-disubstituted piperidines give singlet, while that of trans-isomers give the AB quartet. See: (a) Takahata, H.; Takahashi, S.; Kouno, S.; Momose, T. J. Org. Chem. 1998, 63, 2224. (b) Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H. Org. Lett. 2002, 4, 3459. (c) Harusawa, S.; Sibata, N.; Yamazaki, N.; Sakanoue, S.; Ishida, T.; Yoneda, R.; Kurihara, T. Chem. Pharm. Bull. 1989, 37, 2647.
26. 1H NMR data showed similarity with the related 2,6-disubstituted piperidines. In general, the signals due to the N-benzylic hydrogen of cis-2,6-disubstituted piperidines give singlet, while that of trans-isomers give the AB quartet. See: (a) Takahata, H.; Takahashi, S.; Kouno, S.; Momose, T. J. Org. Chem. 1998, 63, 2224. (b) Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H. Org. Lett. 2002, 4, 3459. (c) Harusawa, S.; Sibata, N.; Yamazaki, N.; Sakanoue, S.; Ishida, T.; Yoneda, R.; Kurihara, T. Chem. Pharm. Bull. 1989, 37, 2647.
27. 1H NMR data showed similarity with the related 2,6-disubstituted piperidines. In general, the signals due to the N-benzylic hydrogen of cis-2,6-disubstituted piperidines give singlet, while that of trans-isomers give the AB quartet. See: (a) Takahata, H.; Takahashi, S.; Kouno, S.; Momose, T. J. Org. Chem. 1998, 63, 2224. (b) Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H. Org. Lett. 2002, 4, 3459. (c) Harusawa, S.; Sibata, N.; Yamazaki, N.; Sakanoue, S.; Ishida, T.; Yoneda, R.; Kurihara, T. Chem. Pharm. Bull. 1989, 37, 2647.
28. +): 213.1517. Found: 213.1510.