Asymmetrie conjugate addition of acetylacetone to nitroolefins with chiral organocatalysts derived from both «-amino acids and carbohydrates

European Journal of Organic Chemistry

Volumn , Issue 27, 2009, Pages 4622-4626

  Pu, Xuewei ^a   Li, Penghui ^a   Peng, Fangzhi ^a   Li, Xiaojiao ^a   Zhang, Hongbin ^a   Shao, Zhihui ^a,b  

^a YUNNAN UNIVERSITY   (China)

^b YUNNAN MINZU UNIVERSITY   (China)

Author keywords

Amino acids; Asymmetric catalysis; Carbohydrates; Organocatalysis

Indexed keywords

EID: 70349213744     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900547     Document Type: Article

References (45)

1. For recent general reviews on organocatalysis, see: a) A. Don- doni, A. Massi, Angew. Chem. Int. Ed. 2008, 47, 4638-4660;
2. b) D. W C.MacMillan, Nature 2008, 455, 304-308;
3. c) P. I. Dalko, Enantioselective Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH, Weinheim, 2007;
4. d) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. C. Vo, Drug Discovery Today 2007, 12, 8-27;
5. e) B. List, J.W Yang, Science 2006, 313, 1584-586;
6. f) A. Berkessel, H. Groger, Asymmetric Organocatalysis - From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005;
7. g) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138-5175.
8. a) F. Peng, Z. Shao, B. Fan, H. Song, G. Li, H. Zhang, J. Org. Chem. 2008, 73, 5202-5205;
9. b) F. Peng, Z. Shao, X. Pu, H. Zhang, Adv. Synth. Catal. 2008, 350, 2199-2204.
10. S. Hanessian, Z. Shao, J. S. Warrier, Org. Lett. 2006, 8, 4787-4790.
11. For a review, see: F. Peng, Z. Shao, J. Mol. Catal. A 2008, 285, 1-13.
12. For selected examples, see: a) J.Liu, Z. Yang, Z. Wang, F. Wang, X. Chen, X. Liu, X. Feng, Z. Su, C.Hu, J.Am. Chem. Soc. 2008, 130, 5654-5655;
13. b) S. S. V. Ramasastry, K. Albertshofer, N. Utsumi, C. F. Barbas III, Org. Lett. 2008, 10, 1621-1624;
14. c) L. Cheng, X. Han, H. Huang, M. W Wong, Y Lu, Chem. Commun. 2007, 4143-4145.
15. a) C. Becker, C. Hoben, H. Kunz, Adv. Synth, Catal, 2007, 349, 417-424;
16. b) K. Liu, H. Cui, J. Nie, K. Dong, X. Li, J. Ma, Org. Lett. 2007, 9, 923-925;
17. c) C. Wang, Z. Zhou, C. Tang, Org. Lett. 2008, 10, 1707-1710.
18. For recent reviews on tertiary amine.....(thio)urea derivatives, see: a) S. J. Connon, Chem. Commun, 2008, 2499-2510;
19. b) Y Takemoto, H. Miyabe, Chimia 2007, 61, 269-275;
20. c) M. S. Taylor, E.N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520-1543.
21. For other types of thiourea catalysts, see: d) C. Cao, M. Ye, X. Sun, Y. Tang, Org. Lett. 2006, 8, 2901-2904;
22. e) Y. Cao, Y. Lai, X. Wang, Y. Li, W Xiao, Tetrahedron Lett. 2007, 48, 21-24;
23. f) Y. Chang, J. Yang, J.Dang, Y. Xue, Synlett 2007, 2283-2285;
24. g) Y. Sohtome, Y. Hashimoto, K. Nagasawa, Adv. Synth. Catal. 2005, 347, 1643-1648;
25. h) S. B. Tsogoeva, D. A. Yalalov, M. J.Hateley, C. Weckbecker, K. Huthmacher, Eur. J. Org. Chem. 2005, 4995-5000.
26. For recent reviews on the asymmetric conjugate addition of nitroolefins, see: a) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716;
27. b) D. Almasi, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2007, 18, 299-365;
28. c) J. L. Vicario, D. Badia, L. Carrillo, Synthesis 2007, 2065-2092;
29. d) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894.
30. For selected examples on organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to nitroolefins, see: a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc 2003, 125, 12672-12673;
31. b) H. Li, Y Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906-9907;
32. c) J. Wang, H. Li, W Duan, L. Zu, W. Wang, Org. Lett. 2005, 7, 4713-4716;
33. d) S. H. McCooey, S. J. Connon, Angew. Chem. Int. Ed. 2005, 44, 6367-6370;
34. e) H. Li, Y. Wang, L. Tang, F Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. Int. Ed. 2005, 44, 105-109;
35. f) M. Terada, H. Ube, Y Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454-1455;
36. g) J. M. Andres, R. Manzano, R. Pedrosa, Chem. Ew. J. 2008, 14, 5116-5119;
37. h) J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416-14417;
38. i) C. Wang, Z. Zhang, X. Dong, X. Wu, Chem, Commun. 2008, 1431-1433;
39. j) X. Li, K. Liu, H. Ma, J. Nie, J. Ma, Synlett 2008 3242-3246;
40. k) P. Gao, C. Wang, Y. Wu, Z. Zhou, C. Tang, Eur. J. Org. Chem. 2008, 4563-4566;
41. J.Luo, L. Xu, R. A. S. Hay, Y. Lu, Org. Lett. 2009, 11, 437-440;
42. m) J. Lubkoll, H. Wennemers, Angew. Chem. Int. Ed. 2007, 46, 6841-14844 See also ref. 2a.
43. I. Coldham, P. O'Brien, J. J. Patel, S. Raimbault, A. J.Sanderson, D. Stead, D. T. E. Whittaker, Tetrahedron: Asymmetry 2007, 18, 2113-2119.
44. M. J. Camarasa, P. Fernandez-Resa, M. T. Garcia Lopez, F'. G. Delas Heras, P. P. Mendez Castrillon, A. S. Felix, Synthesis 1984, 509-510.
45. Absolute configurations of compounds 6a-g were determined by comparing the HPLC retention times of the products with those given in the literature.