Asymmetrie Michael addition of γ,γ-disubstituted α,β-unsaturated aldehydes to nitroolefins via dienamine catalysis

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4660-4663

  Han, Bo ^a   Xiao, You Cai ^a   He, Zhao Quan ^a   Chen, Ying Chun ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; AMINE;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; ALKENES; AMINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 70349898269     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901939b     Document Type: Article

References (44)

1. Caner, H.; Groner, E.; Levy, L. Drug Discovery Today 2004, 9, 105.
2. For a highlight on scaffold diversity synthesis, see: Galloway. W. R. J. D.; Diáz-Gavilán, M.; Isidro-Liobet, A.; Spring, D. R. Angew. Chem., Int. Ed. 2009, 48, 1194.
3. For selected reviews on asymmetric aminocatalysis, see: (a) Erkkila, A.; Majander, I.: Pihko, P. M. Chem. Rev. 2007, 107, 5416.
4. (b) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
5. (c) Barbas, C. F., III. Angew. Chem., Int. Ed. 2008, 47, 42.
6. (d) Melchiorre, P.; Marigo, M.; Carlone, A.: Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138.
7. (e) Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 1360.
8. (f) Bertelsen, S.: Jørgensen. K. A. Chem. Soc. Rev. 2009, 38, 2178.
9. For selected examples of Michael addition of saturated carbonyl compounds to nitroolefins by enamine catalysis, see: (a) List, B.; Pojarliev, P.: Martin, H. J. Org. Lett. 2001, 3, 2423.
10. (b) Betancort, J. M.: Barbas, C. F. III. Org. Lett. 2001, 3, 3737.
11. (c) Alexakis. A.; Andrey. O. Org. Lett. 2002, 4, 3611.
12. (d) Ishii, T.; Fujioka, S.: Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558.
13. (e) Hayashi, Y.; Gotoh. H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
14. (f) Mase, N.: Watanabe, K.: Yoda, H.; Takabe. K.; Tanaka, F.; Barbas, C F., III. J. Am. Chem. Soc. 2006, 128, 4966.
15. (g) Palomo, C.; Vera. S.; Mielgo, A.; Gómez-Bengoa, E. Chem., Int. Ed. 2006, 45, 5984.
16. (h) Luo, S.: Mi, X.; Zhang, L.: Liu. S.: Xu, H.; Cheng, J.-P. Angew. Chem., Int. Ed. 2006, 45, 3093.
17. (i) McCooev. S. H.; Connon, S. J. Org. Lett. 2007, 9, 599.
18. (j) Liu, K.: Cui, H.-F.; Nie, J.; Dong, K.-Y.; Li, X.-J.; Ma, J.-A. Org. Lett. 2007, 9, 923.
19. (k) Zhu, S.; Yu, S.; Ma, D. Angew. Chem., Int. Ed. 2008, 47, 545.
20. (l) Belot. S.; Sulzer-Mossé, S.; Kehrli, S.; Alexakis, A. Chem. Commun. 2008. 4694.
21. (m) Ruiz, N.; Reyes. E.; Vicario. J. L: Badfa, D.; Carrillo, L.; Uria, U. Chem-Eur. J. 2008, 14, 9357.
22. (n) Tan. B.; Zeng. X.; Lu, Y.; Chua, P. J.: Zhong, G. Org. Lett. 2009, 11, 1927.
23. For a review on the Michael addition of nitroolefins, see: Berner, O. M.: Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
24. For limited examples on dienamine catalysis, see: (a) Ramachary. D. B.: Ramakumar, K. K. Tetrahedron Lett. 2005, 46, 7037.
25. (b) M. Hong, B.-C: Wu. M.-F.: Tseng, H.-C: Liao, J.-H. Org. Lett. 2006, 8, 2217.
26. (c) Bertelsen. S.: Marigo, M.: Brandes, S.; Dinér, P.: Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973.
27. (d) Hong. B.-C: Wu, M.-F.; Tseng, H.-C.; Huang. G.-F.; Su, C.-F.; Liao, J.-H. J. Org. Chem. 2007, 72, 8459.
28. (e) Hong, B.-C.; Tseng. H.-C; Chen, S.-H. Tetrahedron 2007, 63, 2840.
29. (f) de Figueiredo. R. M.; Fröhlich. R.: Christmann. M. Angew. Chem., Int. Ed. 2008, 47, 1450.
30. (g) Marqués-López, E.; Herrera, R. P.; Marks. T.: Jacobs, W. C.; Könning, D.: de Figueiredo. R. M.; Christmann. M. Org. Lett. 2009, 11, 4116.
31. Utsumi. N.; Zhang. H.; Tanaka. F.: Barbas. C F., III. Angew. Chem., Int. Ed. 2007, 46, 1878.
32. Vesely;. J.; Rios, R.: Córdova, A. Tetrahedron Lett. 2008, 49, 1137.
33. Han, B.; He, Z.-Q.; Li, J.-L.: Li, R.: Jiang, K.; Liu, T.-Y.: Chen. Y.-C. Angew. Chem., Int. Ed. 2009, 48, 5474.
34. For reviews on α,α-diarylprolinol ethers catalysis, see: (a) Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876.
35. (b) Yu, X.: Wang, W. Org. Biomol. Chem. 2008, 6, 2037.
36. The absolute configuration of 4a was assigned based on an X-ray structure of the derivative 6e (see Figure 1). Thus, the origin of the stereoselectivity in this dienamine catalysis by catalyst 1 is similar to that observed in its enamine catalysis (see ref 3f).
37. (a) Enders, D.; Hüttl, M. R. M.; Grondai. C.: Raabe, G. Nature 2006, 441, 861.
38. (b) Enders. D.; Hüttl, M. R. M.; Runsink. J.; Raabe, G.; Wendt. B. Angew. Chem., Int. Ed. 2007, 46, 467.
39. (a) Han, B.: Li. J.-L.; Ma, C.: Zhang, S.-J.: Chen, Y.-C. Angew. Chem., Int. Ed. 2008, 47, 9971.
40. (b) Hayashi, Y.; Gotoh, H.; Masui, R.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 4012.
41. (c) Zu, L.: Xie. H.; Li, H.: Wang, J.; Yu, X.; Wang, W. Chem.-Eur. J. 2008, 14, 6333.
42. (a) Nara. S.; Tanaka, R.: Eishima, J.; Hara, M.: Takahashi. Y.: Otaki. S.; Foglesong, R. J.; Hughes, P. F.; Turkington, S.; Kanda, Y. J. Chem. 2003, 46, 2467.
43. (b) Tanaka. R.: Rubio, A.: Harn, N. K.; Gernert, D.; Grese, T. A.: Eishima, J.; Hara, M.: Yoda, N.; Ohashi, R.; Kuwabara, T.; Soga, S.; Akinaga, S.: Naraa, S.; Kanda, Y. Bioorg. Med. Chem. 2007, 15, 1363.
44. Pei, Z.; Li, X.; von Geldern, T. W.; Longenecker, K.; Pireh, D.; Stewart, K. D.: Backes, B. J.; Lai. C.: Lubben, T. H.; Bailaron, S. J.: Beno, D. W. A.: Kempf-Grote, A. J.; Sham. H. L.; Trevillyan, J. M. J. Med. Chem. 2007, 50, 1983.