H. Wu et al. / Tetrahedron Letters 50 (2009) 1062–1065
2. Goswami, S.; Gosh, K.; Disrupt, S. J. Org. Chem. 2000, 65, 1907–1914.
1065
conditions, low catalyst loading, and no formation of by-products
such as aldol or deamination products. In addition, our process in-
volves an environmentally benign, cheap, and easy to handle cata-
lyst. To the best of our knowledge, this is the first report of a TB
derivative-catalyzed direct-type Mannich reaction. Because of its
numerous benefits, the protocol should be very useful in the syn-
thesis of b-aminocarbonyl compounds that might have biological
activities. Application of the optical pure TB derivatives in this kind
of Mannich reaction is under way.
3. Baldeyrou, B.; Tardy, C.; Bailly, C.; Colson, P.; Houssier, C.; Charmantray, F.;
Demeunyck, M. Eur. J. Med. Chem. 2002, 37, 315–322.
4. Tatibouët, A.; Demenunynck, M.; Andraud, C.; Collet, A.; Lhomme, J. Chem.
Commun. 1999, 161–162.
5. Pardo, C.; Sesmilo, E.; Gutiérrez-Puebla, E.; Monge, A.; Elguero, J.; Fruchier, A. J.
Org. Chem. 2001, 66, 1607–1611.
6. Goldberg, Y.; Alper, H. Tetrahedron Lett. 1995, 36, 369–372.
7. Harmata, M.; Kahraman, M. Tetrahedron: Asymmetry 2000, 11, 2875–2879.
8. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221–229.
9. Muller, R.; Goesmann, H.; Waldmann, H. Angew. Chem. 1999, 111, 166–169; .
Angew. Chem., Int. Ed. 1999, 38, 184–187.
10. Wang, Y. G.; Yang, Y. Y.; Shou, W. G. Tetrahedron 2006, 62, 10079–10086.
11. Wang, Y. G.; Yang, Y. Y.; Shou, W. G. Tetrahedron Lett. 2006, 47, 1845–1847.
12. Azizi, N.; Torkiyan, L.; Saidi, M. R. Org. Lett. 2006, 8, 2079–2082.
13. Eftekhari-Sis, B.; Abdollahifa, A.; Hashemi, M. M.; Zirak, M. Eur. J. Org. Chem.
2006, 71, 5152–5157.
14. Ibrahem, I.; Zou, W. B.; Enggvist, M.; Cordova, A. Chem.-Eur. J. 2005, 7024–7029.
15. Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1965–1967.
16. Akiyama, T.; Matsuta, K.; Fuchibe, K. Synlett 2005, 322–324.
17. Matsuda, K.; Mori, Y.; Kobayashi, S. Tetrahedron 2001, 57, 2537–2544.
18. Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1045–1048.
19. Wu, M.; Jing, H. W.; Chang, T. Catal. Commun. 2007, 8, 2217–2221.
20. Wu, H.; Shen, Y.; Fan, L. Y. Tetrahedron 2007, 63, 2404–2408.
21. Bigdeli, M. A.; Nemati, F.; Mahdavinia, G. H. Tetrahedron Lett. 2007, 48, 6801–
6804.
Acknowledgments
We are grateful to the foundation of the ‘National Natural Sci-
ences Foundation of China’ (No. 20772103), ‘Natural Sciences
Foundation of Jiangsu Province’ (No. BK2007028), and the ‘Surpass-
ing Project in Jiangsu Province’ (No. QL200607) for financial
support.
Supplementary data
22. Rosenau, T.; Potthast, A. Tetrahedron 2004, 60, 301–306.
23. Wang, R.; Li, B. G.; Huang, T. K.; Shi, L.; Lu, X. X. Tetrahedron Lett. 2007, 48,
2071–2073.
24. Manabe, K.; Mori, Y. Tetrahedron 2001, 57, 2537–2544.
25. Wu, H.; Zhang, P.; Shen, Y.; Zhang, F. R.; Wan, Y.; Shi, D. Q. Synlett 2007, 336–
338.
Supplementary data associated with this article can be found, in
References and notes
26. Ollevier, T.; Nadeau, E. J. Org. Chem. 2004, 69, 9292–9295.
1. Tröger, J. J. Prakt. Chem. 1887, 36, 225.