Chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction

Journal of the American Chemical Society

Volumn 129, Issue 13, 2007, Pages 3790-3791

  Guo, Qi Xiang ^b,c   Liu, Hua ^b,c   Guo, Chang ^a   Luo, Shi Wei ^a   Gu, Yi ^a   Gong, Liu Zhu ^a,b  

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

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BRONSTED ACID;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRESS; MANNICH REACTION;

ACIDS; CATALYSIS; KETONES; MANNICH BASES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 34247112829     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068236b     Document Type: Article

References (50)

1. For reviews, see: (a) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; pp 923-961.
2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
3. Córdova, A. Acc. Chem. Res. 2004, 37, 102.
4. (a) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995.
5. (b) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
6. (c) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
7. (d) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem., Int. Ed. 2005, 44, 1525.
8. (a) Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.
9. (b) Poulsen, T. B.; Alemparte, C.; Saaby, S.; Bella, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 2896.
10. (c) Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
11. (d) Tillman, A. L.; Ye J.; Dixon, D. J. Chem. Commun. 2006, 1191.
12. (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336.
13. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
14. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
15. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866.
16. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923.
17. (f) Watanabe, S.-i.; Córdova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519.
18. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677.
19. (h) Cobb, J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558.
20. (i) Ibrahem, I.; Casas, J.; Córdova, A. Angew. Chem., Int. Ed. 2004, 43, 6528.
21. (j) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199.
22. (k) Westermann, B.; Neuhaus, C. Angew. Chem., Int. Ed. 2005, 44, 4077.
23. (l) Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed. 2005, 44, 4079.
24. (a) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
25. (b) Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 16408.
26. (c) Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 1040.
27. (d) Zhang, H.; Mifsud, M.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 9630.
28. (e) During revision of this paper, Barbas reported an anti-selective Mannich reaction of aromatic aldimines with ketones catalyzed by primary amino acids: Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2007, 129, 288.
29. For recent excellent reviews, see: (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
30. (b) Connon, S. J. Angew. Chem., Int. Ed. 2006, 45, 3909.
31. (c) Akiyama, A.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
32. For pioneering works, see: (a) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
33. (b) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
34. For recent examples, see: (c) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
35. (d) Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2006, 45, 2254.
36. (e) Rueping, M.; Sugiono, E.; Azap, C. Angew. Chem., Int. Ed. 2006, 45, 2617.
37. (f) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
38. (g) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368.
39. (h) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070.
40. (i) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
41. (j) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
42. (k) Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2006, 45, 4796.
43. (l) Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074.
44. (m) Chen, X.-H.; Xu, X.-Y.; Liu, H.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2006, 128, 14802.
45. (a) Mannich, C.; Krosche, W. Arch. Pharm. 1912, 250, 647.
46. (b) Akiyama, T.; Matsuda, K.; Fuchibe, K. Synlett 2005, 322.
47. (a) Liu, H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Org. Lett. 2006, 8, 6023.
48. (b) Rueping, M.; Azap, C. Angew. Chem., Int. Ed. 2006, 45, 7832.
49. The syn-Mannich product was mainly observed for a similar reaction of 3-pentanone (50% yield, 86/14 dr, 20% ee) probably due to the favorable formation of the Z-enol during reaction.
50. For similar reactions catalyzed by transition metals, see: Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307 and refs 4b,c.