Indium-mediated one-pot three-component reaction of aromatic amines, enol ethers, and allylic bromides

Organic Letters

Volumn 8, Issue 2, 2006, Pages 195-198

  Jang, Taeg Su ^a,b   Ku, Il Whea ^a,b   Jang, Min Seok ^a   Keum, Gyochang ^a   Kang, Soon Bang ^a   Chung, Bong Young ^b   Kim, Youseung ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544471138     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052326o     Document Type: Article

References (27)

1. (a) Ovaa, H.; Stragies, R.; van der Marel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502.
2. (b) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
3. (a) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
4. (b) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
5. Vargas M., L. Y.; Castelli, M. V.; Kouznetsov, V. V.; Urbina G., J. M.; Lopez, S. N.; Sortino, M.; Enriz, R. D.; Ribas, J. C.; Zacchino, S. Bioorg. Med. Chem. 2003, 11, 1531-1550.
6. Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595-614.
7. (a) Giammaruco, M.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1993, 34, 3635-3638.
8. (b) Kobayashi, S.; Busujima, T.; Nagayama, S. Chem. Commun. 1998, 19-20.
9. (c) Akiyama, T.; Iwai, J. Synlett 1998, 273-274.
10. (d) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323-326.
11. (e) Choudary, B. M.; Chidara, S. Sekhar, Ch. V. R. Synlett 2002, 1694-1696.
12. (a) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149-11176.
13. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633-655.
14. For recent examples of indium-mediated allylation of imines and C=N systems, see: (c) Vilaivan, T.; Winotapan, C.; Banphavichit, V.; Shinada, T.; Ohfune, Y. J. Org. Chem. 2005, 70, 3464-3471.
15. (d) Cook, G. R.; Maity, B. C., Kargbo, R. Org. Lett. 2004, 6, 1741-1743 and references therein.
16. (a) Babu, G.; Perumal, P. T. Aldrichimica Acta 2000, 33, 16-18.
17. (b) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347-2356.
18. (a) Kang, S.; Jang, T.-S.; Keum, G.; Kang, S. B.; Han, S.-Y.; Kim, Y. Org. Lett. 2000, 2, 3615-3617.
19. (b) Park, L.; Keum, G.; Kang, S. B.; Kim, K. S.; Kim, Y. J. Chem. Soc., Perkin Trans. 1 2000, 4462-4463.
20. (c) Cho, S.; Keum, G.; Kang, S. B.; Han, S.-Y.; Kim, Y. J. Org. Chem. 2003, 68, 180-182.
21. (d) Jang, T.-S.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Synthesis 2003, 775-779.
22. +, 7.8), 120 (100), 104 (4.3), 91 (3.4), 77 (12.0).
23. Yagoub, A. K.; Iskander, G. M. J. Chem. Soc., Perkin Trans. 1 1977, 697-699.
24. Issac, M. B.; Chan, T. H. Tetrahedron Lett. 1995, 36, 8957-8960.
25. (a) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589-8594.
26. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467-3473.
27. An in situ generation of iminium salt from N,O-acetal: Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 355-396.