A chiral bis(betaine) catalyst for the mannich reaction of azlactones and aliphatic imines

Angewandte Chemie - International Edition

Volumn 51, Issue 17, 2012, Pages 4085-4088

  Zhang, Wen Quan ^a   Cheng, Ling Feng ^a   Yu, Jie ^a   Gong, Liu Zhu ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Br nsted base; heterocycles; imines; organocatalysis; synthetic methods

Indexed keywords

AZLACTONES; BROAD SPECTRUM; CATALYTICALLY ACTIVE CENTERS; DIAMINO ACIDS; HETEROCYCLES; IMINES; MANNICH REACTIONS; MANNICH-TYPE REACTIONS; ORGANOCATALYSIS; ORGANOCATALYSTS; SYNTHETIC METHODS;

REACTION KINETICS;

NITROGEN COMPOUNDS;

EID: 84859974250     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107741     Document Type: Article

References (57)

1. R. Noyori, Asymmetric Catalysis in organic Synthesis, Wiley, New York, 1994
2. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999
3. A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
4. B. List, Asymmetric Organocatalysis (Top. Curr. Chem.), Springer, Berlin, 2010, 291
5. Q.-L. Zhou, Privileged Chiral Ligands and Catalysts, Wiley-VCH, Weinheim, 2011.
6. S. Piovesana, D. M. ScarpinoSchietroma, M. Bella, Angew. Chem. 2011, 123, 6340
7. Angew. Chem. Int. Ed. 2011, 50, 6216.
8. M. Shibasaki, M. Kanai, S. Matsunaga, N. Kumagai, Acc. Chem. Res. 2009, 42, 1117.
9. B. M. Trost, H. Ito, E. R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367.
10. R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780.
11. Q.-X. Guo, Z.-J. Wu, Z.-B. Luo, Q.-Z. Liu, J.-L. Ye, S.-W. Luo, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2007, 129, 13927.
12. W. Hirahata, R. M. Thomas, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2008, 130, 17658.
13. S. C. Pan, B. List, Chem. Asian J. 2008, 3, 430
14. D. Kampen, A. Ladépêche, G. Claßen, B. List, Adv. Synth. Catal. 2008, 350, 962.
15. M. Hatano, T. Maki, K. Moriyama, M. Arinobe, K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858.
16. T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 10054.
17. R. Chinchilla, P. Mazón, C. Nájera, Tetrahedron: Asymmetry 2002, 13, 927.
18. H.-g. Park, B.-S. Jeong, M.-S. Yoo, J.-H. Lee, M.-k. Park, Y.-J. Lee, M.-J. Kim, S.-s. Jew, Angew. Chem. 2002, 114, 3162
19. Angew. Chem. Int. Ed. 2002, 41, 3036
20. M. Q. Hua, H. F. Cui, L. Wang, J. Nie, J. A. Ma, Angew. Chem. 2010, 122, 2832
21. Angew. Chem. Int. Ed. 2010, 49, 2772.
22. X.-H. Chen, W.-Q. Zhang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 5652.
23. D. Uraguchi, K. Koshimoto, T. Ooi, J. Am. Chem. Soc. 2008, 130, 10878
24. D. Uraguchi, K. Koshimoto, S. Miyake, T. Ooi, Angew. Chem. 2010, 122, 5699
25. Angew. Chem. Int. Ed. 2010, 49, 5567
26. D. Uraguchi, K. Koshimoto, T. Ooi, Chem. Commun. 2010, 46, 300.
27. N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094.
28. A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336
29. N. Momiyama, Y. Yamamoto, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 1190.
30. H.-F. Du, D.-B. Zhao, K.-L. Ding, Chem. Eur. J. 2004, 10, 5964
31. X. Zhang, H.-F. Du, Z. Wang, Y.-D. Wu, K.-L. Ding, J. Org. Chem. 2006, 71, 2862.
32. S. Schenker, A. Zamfir, M. Freund, S. B. Tsogoeva, Eur. J. Org. Chem. 2011, 2209.
33. C. Cativiela, M. D. Díaz-de-Villegas, Tetrahedron: Asymmetry 1998, 9, 3517
34. Y. Ohfune, T. Shinada, Bull. Chem. Soc. Jpn. 2003, 76, 1115
35. A. Viso, R. F. deLaPradilla, A. García, A. Flores, Chem. Rev. 2005, 105, 3167
36. R. G. Arrayás, J. C. Carretero, Chem. Soc. Rev. 2009, 38, 1940.
37. A. Córdova, Acc. Chem. Res. 2004, 37, 102
38. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797
39. J. M. M. Verkade, L. J. C. vanHemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29.
40. D. Uraguchi, Y. Ueki, T. Ooi, J. Am. Chem. Soc. 2008, 130, 14088.
41. Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 2170.
42. K. R. Knudsen, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 1362.
43. A. Singh, J. N. Johnston, J. Am. Chem. Soc. 2008, 130, 5866.
44. B. Han, Q.-P. Liu, R. Li, X. Tian, X.-F. Xiong, J.-G. Deng, Y.-C. Chen, Chem. Eur. J. 2008, 14, 8094.
45. A. Puglisi, L. Raimondi, M. Benaglia, M. Bonsignore, S. Rossi, Tetrahedron Lett. 2009, 50, 4340.
46. J. Clayden, P. MacLellan, Beilstein J. Org. Chem. 2011, 7, 582
47. C. Rissing, D. Y. Son, Main Group Chem. 2009, 8, 251
48. A. M. Masdeu-Bultó, M. Diéguez, E. Martin, M. Gómez, Coord. Chem. Rev. 2003, 242, 159.
49. H.-M. Cheng, W. Tian, P. A. Peixoto, B. Dhudshia, D. Y.-K. Chen, Angew. Chem. 2011, 123, 4251
50. Angew. Chem. Int. Ed. 2011, 50, 4165
51. C. J. Besset, A. T. Lonnecker, J. M. Streff, K. L. Wooley, Biomacromolecules 2011, 12, 2512
52. T. Xu, C.-C. Li, Z. Yang, Org. Lett. 2011, 13, 2630.
53. O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147
54. N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G. Lohmeijer, J. L. Hedrick, Chem. Rev. 2007, 107, 5813
55. A. Harada, M. Osaki, Y. Takashima, H. Yamaguchi, Acc. Chem. Res. 2008, 41, 1143.
56. S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008, 130, 12031
57. Y. Chai, D. A. Vicic, M. C. Mclntosh, Org. Lett. 2003, 5, 1039.