Water-compatible iminium activation: Highly enantioselective organocatalytic michael addition of malonates to α,β-unsaturated enones

Journal of Organic Chemistry

Volumn 75, Issue 21, 2010, Pages 7428-7430

  Mao, Zhifeng ^a   Jia, Yaomei ^a   Li, Wenyi ^a   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; ENANTIOSELECTIVE MICHAEL ADDITION; IMINIUM; LONG ALKYL CHAINS; MALONATES; MICHAEL ADDITIONS; ORGANOCATALYTIC; UNSATURATED KETONES;

KETONES;

ADDITION REACTIONS;

ALKYL GROUP; CHALCONE DERIVATIVE; DIAMINE DERIVATIVE; KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; MICHAEL ADDITION; SYNTHESIS;

ALKENES; CATALYSIS; IMINES; KETONES; MALONATES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; WATER;

EID: 78049489759     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101188m     Document Type: Article

References (66)

1. Grieco, P. A., Ed. Organic Synthesis in Water; Blackie: London, 1998.
2. Lindstrom, U. M. Chem. Rev. 2002, 102, 2751
3. Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209
4. Li, C.-J. Chem. Rev. 2005, 105, 3095
5. Pirrung, M. C. Chem.-Eur. J. 2006, 12, 1312
6. Mase, N.; Barbas, C. F., III. Org. Biomol. Chem. 2010, 8, 4043
7. For some selected examples of aldol reactions in aqueous media: Dickerson, T. J.; Janda, K. D. J. Am. Chem. Soc. 2002, 124, 3220
8. Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983
9. Hayashi, Y.; Aratake, S.; Okano, T.; Takahashi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 5527
10. Font, D.; Jimeno, C.; Pericàs, M. A. Org. Lett. 2006, 8, 4653
11. Wu, Y.; Zhang, Y.; Yu, M.; Zhao, G.; Wang, S. Org. Lett. 2006, 8, 4417
12. Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 734 Mannich reaction: Cheng, L.; Wu, X.; Lu, Y. Org. Biomol. Chem. 2007, 5, 1018
13. Hayashi, Y.; Urushima, T.; Aratake, S.; Okano, T.; Obi, K. Org. Lett. 2008, 10, 21
14. Amedjkouh, M.; Brandberg, M. Chem. Commun. 2008, 3043 For some selected examples of Michael reactions: Mase, N.; Watanabe, K.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 4966
15. Zu, L.; Wang, J.; Li, H.; Wang, W. Org. Lett. 2006, 8, 3077
16. Luo, S.; Mi, X.; Liu, S.; Xu, H.; Cheng, J.-P. Chem. Commun. 2006, 3687
17. Carlone, A.; Marigo, M.; North, C.; Landa, A.; Jørgensen, K. A. Chem. Commun. 2006, 4928
18. Singh, V.; Singh, V. K. Org. Lett. 2007, 9, 1117
19. Zhu, S. L.; Yu, S. Y.; Ma, D. W. Angew. Chem., Int. Ed. 2008, 47, 545
20. Palomo, C.; Landa, A.; Mielgo, A.; Oiarbide, M.; Puente, Á.; Vera, S. Angew. Chem., Int. Ed. 2007, 46, 8431
21. Belot, S.; Massaro, A.; Tenti, A.; Mordini, A.; Alexakis, A. Org. Lett. 2008, 10, 4557
22. Wang, J.; Yu, F.; Zhang, X.; Ma, D. Org. Lett. 2008, 10, 2561
23. Zheng, Z.; Perkins, B. L.; Ni, B. J. Am. Chem. Soc. 2010, 132, 50 for a recent review
24. Raj, M.; Singh, V. K. Chem. Commun. 2009, 6687
25. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
26. Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1.
27. Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033
28. Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569.
29. Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171
30. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
31. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701
32. Vicario, J. L.; Badía, D.; Carrillo, L. Synthesis 2007, 2065
33. Almaşi, D.; Alonso, D. A.; Nájera, C. Tetrahedron: Asymmetry 2007, 18, 299
34. Northrup, A. B.; D. MacMillan, W. C. J. Am. Chem. Soc. 2002, 124, 2458
35. For selected examples, see: Reisinger, C. M.; Wang, X.; List, B. Angew. Chem., Int. Ed. 2008, 47, 8112
36. Xie, J.-W.; Yue, L.; Chen, W.; Du, W.; Zhu, J.; Deng, J.-G.; Chen, Y.-C. Org. Lett. 2007, 9, 413
37. Liu, T.-Y.; Cui, H.-L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z.- Q.; Chen, Y.-C. Org. Lett. 2007, 9, 3671
38. Chen, W.; Du, W.; Duan, Y.-Z.; Wu, Y.; Yang, S.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2007, 46, 7667
39. Wang, X.; Reisinger, C. M.; List, B. J. Am. Chem. Soc. 2008, 130, 6070
40. Singh, R. P.; Bartelson, K.; Wang, Y.; Su, H.; Lu, X.; Deng, L. J. Am. Chem. Soc. 2008, 130, 2422
41. Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389
42. Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134 For some leading reviews, see: Xu, L.-W.; Lu, Y.-X. Org. Biomol. Chem. 2008, 6, 2047
43. Chen, Y.-C. Synlett 2008, 1919
44. Bartoli, G.; Melchiorre, P. Synlett 2008, 1759
45. Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520
46. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. 1993, 32, 1176
47. For recent examples: Park, S.-Y.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Tetrahedron Lett. 2007, 48, 2815
48. Chen, C.; Zhu, S.-F.; Wu, X.-Y.; Zhou, Q.-L. Tetrahedron: Asymmetry 2006, 17, 2761
49. Kumaraswamy, G.; Jena, N.; Sastry, M. N. V.; Rao, G. V.; Ankamma, K. J. Mol. Catal. A 2005, 230, 59
50. Agostinho, M.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 2430
51. Naka, H.; Kanase, N.; Ueno, M.; Kondo, Y. Chem.-Eur. J. 2008, 14, 5267
52. Chen, D.; Chen, Z.; Xiao, X.; Yang, Z.; Lin, L.; Liu, X.; Feng, X. Chem.-Eur. J. 2009, 15, 6807
53. Wang, Z.; Wang, Q.; Zhang, Y.; Bao, W. Tetrahedron Lett. 2005, 46, 4657
54. Ooi, T.; Ohara, D.; Fukumoto, K.; Maruoka, K. Org. Lett. 2005, 7, 3195
55. Dere, R. T.; Pal, R. R.; Patil, P. S.; Salunkhe, M. M. Tetrahedron Lett. 2003, 44, 5351
56. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299
57. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661
58. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272
59. Wang, J.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Duan, W.; Wang, W. J. Am. Chem. Soc. 2006, 128, 12652
60. Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V. Chem. Commun. 2006, 66
61. Wascholowski, V.; Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V. Chem.-Eur. J. 2008, 14, 6155
62. Jiang, Z.; Ye, W.; Yang, Y.; Tan, C.-H. Adv. Synth. Catal. 2008, 350, 2345
63. Yang, Y.-Q.; Zhao, G. Chem.-Eur. J. 2008, 14, 10888
64. Li, P.; Wen, S.; Yu, F.; Liu, Q.; Li, W.; Wang, Y.; Liang, X.; Ye, J. Org. Lett. 2009, 11, 753
65. Yang, Y.-Q.; Chai, Z.; Wang, H.-F.; Chen, X.-K.; Cui, H.-F.; Zheng, C.-W.; Xiao, H.; Li, P.; Zhao, G. Chem.-Eur. J. 2009, 15, 13295
66. Hong, L; Sun, W.; Liu, C.; Wang, L.; Wong, K.; Wang, R. Chem.-Eur. J. 2009, 15, 11105