Enantioselective Michael addition of aromatic ketones to nitroolefins catalyzed by bifunctional thioureas and mechanistic insight

European Journal of Organic Chemistry

Volumn , Issue 4, 2010, Pages 656-662

  Li, Bai Lin ^a,b   Wang, Yi Feng ^a   Luo, Shu Ping ^a   Zhong, Ai Guo ^b   Li, Zhao Bo ^a   Du, Xiao Hua ^a   Xu, Dan Qian ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b TAIZHOU UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; Michael addition; Organocatalysis; Reaction mechanisms

Indexed keywords

EID: 74949127376     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900932     Document Type: Article

References (83)

1. For an overview of asymmetric organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed, 2004, 43, 5138-5175;
2. b) T. Marcelli, J. H. Van Maarseveen, H. Hiemstra, Angew. Chem. Int. Ed. 2006, 45, 7496-7504;
3. M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001-2011;
4. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
5. e) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. T. Vo, Drug Discovery Today 2007, 12, 8-27;
6. f) A. Erkkil, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416-5470;
7. g) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569;
8. h) M. J. Gaunt, C. C. C. Johansson, Chem. Rev. 2007, 107, 5596-5605;
9. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606-5655;
10. j) T. Hashimoto, K. Maruoka, Chem. Rev. 2007, 107, 5656-5682;
11. k) T. Akiyama, Chem. Rev. 2007, 107, 5744-5758;
12. l) N. Marion, S. DíezGonzález, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 2988-3000;
13. A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 2008, 47, 4638 -4660;
14. n) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. Int. Ed. 2008, 47, 6138-6171;
15. o) D. W. D. MacMillan, Nature 2008, 455, 304-308;
16. p) V. Nair, S. Vellalath, B. P. Babu, Chem, Soc. Rev. 2008, 37, 2691-2698;
17. q) S. J. Connon, Chem. Commun. 2008, 2499-2510;
18. r) C. Palomo, M. Oiarbide, R. López, Chem. Soc. Rev. 2009, 38, 632-653.
19. For an overview of asymmetric Michael additions, see: a) J. Christoffers, Eur. J. Org. Chem. 1998, 7, 1259 - 1266;
20. b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171 - 196;
21. O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877 - 1894;
22. J. Christoffers in Encyclopedia of Catalysis (Eds.: I. Horvath), Wiley, New York, 2002, vol.5, pp. 99 - 118;
23. e) L.- W. Xu, C.-G. Xia, Eur. J. Org. Chem. 2005, 633-639;
24. f) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716;
25. g) S. SulzerMossé, A. Alexakis, Chem. Commun. 2007, 3123-3135;
26. h) D. Almasi, D. A. Alonso, C Nájera, Tetrahedron: Asymmetry 2007, 18, 299-365;
27. i) C. F. Nising, S. Bräse, Chem. Soc. Rev. 2008, 37, 1218-1228.
28. For typical examples of Michael additions of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by amine-thiourea bifunctional catalysts, see: a) T Okino, Y Hoashi, Y Takemoto, J. Am. Chem. Soc. 2003, 125, 12672 - 12673;
29. b) S. H. McCooey, S. J. Connon, Angew. Chem. Int. Ed. 2005, 44, 6367 - 6370;
30. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119 - 125;
31. J.-X. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun. 2005, 4481-4483;
32. e) J. Wang, H. Li, W-H. Duan, L.-S. Zu, W. Wang, Org. Lett. 2005, 7, 4713 - 4716;
33. f) T. Inokuma, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2006,128, 9413 - 9419;
34. g) J. Lubkoll, D. Chem, H. Wennemers, Angew. Chem. Int. Ed. 2007, 46, 6841 - 6844;
35. h) J. M. Andrés, R. Manzano, R. Pedrosa, Chem. Eur. J. 2008, 14, 5116 - 5119;
36. i) F.-Z. Peng, Z.-H. Shao, B.-M. Fan, H. Song, G.-P. Li, H.-B. Zhang, J. Org. Chem. 2008, 73, 5202-5205.
37. a) J. M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, C. F. Barbas, Synthesis 2004, 1509 - 1521;
38. b) C. E. T. Mitchell, A. J. A. Cobb, S.V. Ley, Synlett 2005, 611 - 614;
39. S. B. Tsogoeva, D. A. Yalalov, M. J. Hateley, C. Weckbecker, K. Huthmacher, Eur. J. Org. Chem. 2005, 4995 - 5000;
40. d) P. S. Hynes, D. Stranges, P. A. Stupple, A. Guarna, D. J. Dixon, Org. Lett. 2007, 9, 2107-2110.
41. [5] a) J. Lin, H.-T. Zheng, T.-Y. Liu, Y. Lei, Y.-C. Chen, Tetrahedron 2007, 63, 5123 - 5128;
42. b) S. H. Peter, A. S. Paul, J. D. Darren, Org. Lett. 2008, 10, 1389 - 1391;
43. C. -J. Wang, Z.-H. Zahng, X.-Q. Dong, X.-J. Wu, Chem. Commun. 2008, 1431-1433.
44. For examples of asymmetric organocatalysis based on the primary amine functionality, see: a) S. Pizzarello, A. L. Weber, Science 2004, 303, 1151;
45. b) F. Tanaka, R. Thayumanavan, N. Mase, C. F. Barbas III, Tetrahedron Lett. 2004, 45, 325 - 328;
46. S. B. Tsogoeva, S. B. Jagtap, Synlett 2004, 2624 - 2626;
47. S. B. Tsogoeva, S. B. Jagtap, Z. A. Ardemasova, V. N. Kalikhevich, Eur. J. Org. Chem. 2004, 4014 - 4019;
48. e) S. B. Tsogoeva, S. Wei, Tetrahedron: Asymmetry 2005, 16, 1947 - 1951;
49. f) M. Amedjk ouh, Tetrahedron: Asymmetry 2005, 16, 1411 - 1414;
50. g) A. Bas- san, W. Zou, E. Reyes, F. Himo, A. Córdova, Angew. Chem. 2005, 117, 7190 - 7194;
51. Angew. Chem. Int. Ed. 2005, 44, 7028 - 7032;
52. h) A. Córdova, W Zou, I. Ibrahem, E. Reyes, M. Engqvist, W.-W. Liao, Chem. Commun. 2005, 3586-3588;
53. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504-10505;
54. j) A. Sakakura, K. Suzuki, K. Nakano, K. Ishihara, Org. Lett. 2006, 8, 2229-2232;
55. k) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403-1405;
56. l) K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2007, 129, 8930-8931;
57. m) W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007,119, 7811-7814;
58. Angew. Chem. Int. Ed, 2007, 46, 7667-7670;
59. n) S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599-602; for a recent review on organocatalysis by chiral primary amines, see:
60. o) F. Peng, Z. Shao, J. Mol. Catal. A 2008, 285, 1-13.
61. D. J. Hupe in New Comprehensive Biochemistry, Elsevier, Amsterdam, 1984, vol.6, pp. 271-301.
62. a) S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451-1453;
63. b) H. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170-7171;
64. c) M. P. Laloude, Y. Chen, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 6366;
65. D. A. Yalaov, S. B. Tsogoeva, S. Schmatz, Adv. Synth, Catal. 2006, 348, 826-832;
66. e) C.-L. Cao, M.-C. Ye, X.-L. Sun, Y. Tang, Org. Lett. 2006, 8, 2901-2904;
67. f) Y.-J. Cao, Y.-Y. Lai, X. Wang, Y.-J. Li, W-J. Xiao, Tetrahedron Lett. 2007, 48, 21-24;
68. g) W.-W. Sheng, D. A. Yalaov, S. B. Tsogoeva, S. Schmatz, Catal. Today 2007,121, 151- 157;
69. h) X.-J. Zhang, S.-P. Liu, X.-M. Li, M. Yan, A. S. C. Chan, Chem. Commun. 2009, 833-835.
70. a) K. Liu, H.-F. Cui, J. Nie, K.-Y. Dong, X.-J. Li, J.-A. Ma, Org. Lett. 2007, 9, 923 - 925;
71. b) X.-X. Jiang, Y. F. Zhang, S. Albert, C. Chan, R. Wang, Org. Lett. 2009, 11, 153 - 156;
72. C. G. Kokotos, G. Kokotos, Adv. Synth. Catal. 2009, 351, 1355-1362.
73. a) D.-Q. Xu, H.-D. Yue, S.-P. Luo, A.-B. Xia, S. Zhang, Z.-Y. Xu, Org. Biomol. Chem. 2008, 6, 2054-2057;
74. b) D.-Q. Xu, L.P. Wang, S.-P. Luo, Y.-F. Wang, S. Zhang, Z.-Y. Xu, Eur. J. Org. Chem, 2008, 1049-1053;
75. D.-Q. Xu, S.-P. Luo, Y.-F. Wang, A.-B. Xia, H.-D. Yue, L.-P. Wang, Z.-Y. Xu, Chem. Commun. 2007, 4393-4395;
76. D.-Q. Xu, Y.-F. Wang, S.-P. Luo, S. Zhang, Z.-Y. Xu, Adv. Synth. Catal, 2008, 350, 2610-2616.
77. a) T. J. Peelen, Y. Chi, S. H. Gellman, J. Am. Chem. Soc, 2005, 127, 11598-11599;
78. b) Y. Chi, L. Guo, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc. 2008, 130, 5608-5609.
79. CCDC-720535 contains the crystallographic data for this paper. These data can be obtained free of charge from The Cam- bridge Cristallographic Data Centre via www.ccdc.cam.ac.uk/data.-request/cif.
80. C. Marquez, J. O. Metzger, Chem. Commun. 2007, 1539-1541.
81. C. A. Marques, F. Fabbretti, J. O. Metzger, Angew. Chem. Int. Ed. 2007, 46, 6915-6917.
82. W Schrader, P. P. Handayani, C. Burstein, F. Glorius, Chem. Commun. 2007, 716-718.
83. W Schrader, P. P. Handayani, I Zhou, B. List, Angew. Chem. Int. Ed. 2009, 48, 1463-1466.