Cinchona alkaloid-catalyzed asymmetric direct mannich reaction of malononitrile to imine for synthesis of β-amino malononitrile

Chinese Journal of Chemistry

Volumn 30, Issue 10, 2012, Pages 2333-2337

  Lu, Zhijin ^a   Xie, Chen ^a   Zhou, Wei ^a   Duan, Zhiqiang ^a   Han, Jianlin ^a   Pan, Yi ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

amino Malononitrile; asymmetric Mannich reaction; cinchona alkaloids; imines

Indexed keywords

EID: 84867830237     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201200586     Document Type: Article

References (35)

1. Nemoto, H.,;, Ma, R.,;, Kawamura, T.,;, Kamiya, M.,;, Shibuya, M.,. J. Org. Chem., 2006, 71, 6038.
2. Nemoto, H.,;, Ma, R.,;, Moriguchi, H.,;, Suzuki, I.,;, Shibuya, M.,. J. Organomet. Chem., 2000, 611, 445.
3. Nemoto, H.,;, Moriguchi, H.,;, Ma, R.,;, Kawamura, T.,;, Kamiya, M.,;, Shibuya, M.,. Tetrahedron: Asymmetry, 2007, 18, 383.
4. Nemoto, H.,;, Kubota, Y.,;, Yamamoto, Y.,. J. Org. Chem., 1990, 55, 4515.
5. Levitzki, A.,;, Gilon, C.,;, Chorev, M.,;, Gazit, A.,. EP 0322738 Chem. Abstr., 1989, 122, 172316.
6. Gorulya, A. P.,;, Tverdokhlebov, A. V.,;, Tolmachev, A. A.,;, Shishkin, O. V.,;, Shishkina, S. V.,. Tetrahedron, 2011, 67, 1030.
7. Ershov, O. V.,;, Melekhin, E. A.,;, Bardasov, I. N.,;, Kayukov, Y. S.,;, Eremkin, A. V.,;, Nasakin, O. E.,. Russ. J. Org. Chem., 2006, 42, 1380.
8. Palacios, F.,;, Alonso, C.,;, Rubiales, G.,;, Tobillas, C.,;, Ezpeleta, J. M.,. Heterocycles, 2003, 61, 493.
9. Banert, K.,;, Koehler, F.,. Angew. Chem., Int. Ed., 2001, 40, 174.
10. Monge, D.,;, Jensen, K. L.,;, Franke, P. T.,;, Lykke, L.,;, Jørgensen, K. A.,. Chem. Eur. J., 2010, 16, 9478.
11. Yasuda, K.,;, Shindo, M.,;, Koga, K.,. Tetrahedron Lett., 1996, 37, 6343.
12. Chen, Y. C.,;, Xue, D.,;, Deng, J. G.,;, Cui, X.,;, Zhu, J.,;, Jiang, Y. Z.,. Tetrahedron Lett., 2004, 45, 1555.
13. Liu, M.,;, Sibi, M. P.,. Tetrahedron, 2002, 58, 7991.
14. Rigoli, J. W.,;, Boralsky, L. A.,;, Hershberger, J. C.,;, Marston, D.,;, Meis, A. R.,;, Guzei, I. A.,;, Schomaker, J. M.,. J. Org. Chem., 2012, 77, 2446.
15. Kodama, K.,;, Sugawara, K.,;, Hirose, T.,. Chem. Eur. J., 2011, 17, 13584.
16. Vesely, J.,;, Ibrahem, I.,;, Rios, R.,;, Zhao, G. L.,;, Xu, Y. M.,;, Cordova, A.,. Tetrahedron Lett., 2007, 48, 2193.
17. Ting, A.,;, Schaus, S. E.,. Eur. J. Org. Chem., 2007, 5797.
18. Verkade, J. M. M.,;, van Hemert, L. J. C.,;, Quaedflieg, P. J. L. M.,;, Rutjes, F. P. J. T.,. Chem. Soc. Rev., 2008, 37, 29.
19. Arrayás, R. G.,;, Carretero, J. C.,. Chem. Soc. Rev., 2009, 38, 1940.
20. Candeias, N. R.,;, Montalbano, F.,;, Cal, P. M. S. D.,;, Gois, P. M. P.,. Chem. Rev., 2010, 110, 6169.
21. Uraguchi, D.,;, Terada, M.,. J. Am. Chem. Soc., 2004, 126, 5356.
22. Hatano, M.,;, Horibe, T.,;, Ishihara, K.,. J. Am. Chem. Soc., 2010, 132, 56.
23. Masahiro, T.,;, Keiichi, S.,;, Daisuke, U.,. Synlett, 2006, 133.
24. Marigo, M.,;, Kjaersgaard, A.,;, Juhl, K.,;, Gathergood, N.,;, Jorgensen, K. A.,. Chem. Eur. J., 2003, 9, 2359.
25. Song, J.,;, Wang, Y.,;, Deng, L.,. J. Am. Chem. Soc., 2006, 128, 6048.
26. Chen, Z. X.,;, Ai, T.,;, Kaur, P.,;, Li, G.,. Tetrahedron Lett., 2009, 50, 1079.
27. Qian, C. T.,;, Gao, F. F.,;, Chen, R. F.,. Tetrahedron Lett., 2001, 42, 4673.
28. Foresti, E.,;, Palmieri, G.,;, Petrini, M.,;, Profeta, R.,. Org. Biomol. Chem., 2003, 1, 4275.
29. Bernardi, L.,;, Fini, F.,;, Herrera, R. P.,;, Ricci, A.,;, Sgarzani, V.,. Tetrahedron, 2006, 62, 375.
30. Inocuma, T.,;, Hoashi, Y.,;, Takemoto, Y.,. J. Am. Chem. Soc., 2006, 128, 9413.
31. Taylor, M. S.,;, Jacobsen, E. N.,. J. Am. Chem. Soc., 2003, 125, 11204.
32. Taylor, M. S.,;, Zalatan, D. N.,;, Lerchner, A. M.,;, Jacobsen, E. N.,. J. Am. Chem. Soc., 2005, 127, 1313.
33. Hoashi, Y.,;, Okino, T.,;, Takemoto, Y.,. Angew. Chem., Int. Ed., 2005, 44, 4032.
34. Wei, Y.,;, He, W.,;, Liu, Y. L.,;, Liu, P.,;, Zhang, S. Y.,. Org. Lett., 2012, 14, 704.
35. Zhao, M. X.,;, Tang, W. H.,;, Chen, M. X.,;, Wei, D. K.,;, Dai, T. L.,;, Shi, M.,. Eur. J. Org. Chem., 2011, 6078.