Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water

Angewandte Chemie - International Edition

Volumn 47, Issue 3, 2008, Pages 545-548

  Zhu, Shaolin ^a   Yu, Shouyun ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aldehydes; Asymmetric catalysis; Diastereoselectivity; Michael addition; Nitroalkenes

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; AMINES; ENANTIOSELECTIVITY;

DIPHENYLPROLINOL COMPOUNDS; MICHAEL ADDITION; ORGANOCATALYSIS;

CATALYST ACTIVITY;

ALDEHYDE; ALKENE; AMINE; AMINO ACID; NITRO DERIVATIVE; SOLVENT; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKENES; AMINES; AMINO ACIDS; CATALYSIS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; SOLVENTS; STEREOISOMERISM; WATER;

EID: 38949133131     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704161     Document Type: Article

References (62)

1. J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737.
2. For recent reviews, see: a) J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065;
3. b) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
4. c) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
5. Angew. Chem. Int. Ed. 2007, 46, 1570.
6. a) N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527;
7. b) O. Andrey, A. Vidonne, A. Alexakis, Tetrahedron Lett. 2003, 44, 7901;
8. c) O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147;
9. d) W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393;
10. Angew. Chem. Int. Ed. 2005, 44, 1369;
11. e) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
12. Angew. Chem. Int. Ed. 2005, 44, 4212;
13. f) C. E. T. Mitchell, A. J. A. Cobb, S. V. Ley, Synlett 2005, 611;
14. g) Y. Xu, W, Zhou, H. Sundén, I. Ibrahem, A. Córdova, Adv. Synth. Catal. 2006, 348, 418;
15. h) J. Wang, H. Li, B. Lou, L. Zu, H. Guo, W. Wang, Chem. Eur. J. 2006, 12, 4321;
16. i) S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, J.-P. Cheng, Angew. Chem. 2006, 118, 3165;
17. Angew. Chem. Int. Ed. 2006, 45, 3093;
18. j) C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. 2006, 118, 6130;
19. Angew. Chem. Int. Ed. 2006, 45, 5984;
20. k) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966;
21. l) S. Mosse, M. Laars, K. Kriis, T. Kanger, A. Alexakis, Org. Lett. 2006, 8, 2559;
22. m) S. Mosse, A. Alexakis, Org. Lett. 2006, 8, 3577;
23. n) E. Reyes, J. L. Vicario, D. Badia, L. Carrillo, Org. Lett. 2006, 8, 6135;
24. o) S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599;
25. p) M. T. Barros, A. M. F. Phillips, Eur. J. Org. Chem. 2007, 178;
26. q) S. Sulzer-Mossé, A. Alexakis, Chem. Commun. 2007, 3123.
27. For Michael reactions involving tandem processes, see: a) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
28. b) D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471;
29. Angew. Chem. Int. Ed. 2007, 46, 467;
30. c) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
31. Angew. Chem. Int. Ed. 2007, 46, 4922.
32. a) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173;
33. b) D. Seebach, S. Abele, K. Gademann, B. Jaun, Angew. Chem. 1999, 111, 1700;
34. Angew. Chem. Int. Ed. 1999, 38, 1595;
35. c) S. H. Lee, J. S. Park, B. M. Kim, S. H. Gellmann, J. Org. Chem. 2003, 68, 1575.
36. For recent synthetic studies, see: d) M. A. Swiderska, J. D. Stewart, Org. Lett. 2006, 8, 6131;
37. e) H. Huang, X. Liu, J. Deng, Z. Zheng, Org. Lett. 2006, 8, 3359;
38. f) J. E. Beddow, S. G. Davies, A. D. Smith, A. J. Russell, Chem. Commun. 2004, 2778.
39. a) M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 4572;
40. b) R. Fernández, A. Ferrete, J. M. Lassaletta, J. M. Llera, E. Martín-Zamora, Angew. Chem. 2002, 114, 859;
41. Angew. Chem. Int. Ed. 2002, 41, 831, and references therein.
42. a) N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734;
43. b) Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972;
44. Angew. Chem. Int. Ed. 2006, 45, 958;
45. c) D. G. Blackmond, A. Armstrong, V. Coombe, A. Wells, Angew. Chem. 2007, 119, 3872;
46. Angew. Chem. Int. Ed. 2007, 46, 3798.
47. For selected references, see: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260;
48. b) M. Nakadai, S. Saito, H. Yamamoto, Tetrahedron 2002, 58, 8167;
49. c) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474;
50. Angew. Chem. Int. Ed. 2004, 43, 2420;
51. d) Y. Xu, A. Córdova, Chem. Commun. 2006, 460;
52. e) P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029;
53. Angew. Chem. Int. Ed. 2007, 46, 1983.
54. a) Y. Chi, S. H. Gellman, Org. Lett. 2005, 7, 4253;
55. b) B. List, J. Am. Chem. Soc. 2002, 124, 5656.
56. a) R. Ling, I. V. Ekhato, J. R. Rubin, D. J. Wustrow, Tetrahedron 2001, 57, 6579;
57. b) R. Galeazzi, G. Martelli, G. Mobbili, M. Orena, S. Rinaldi, Tetrahedron: Asymmetry 2003, 14, 3353.
58. For recent reviews, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
59. Angew. Chem. Int. Ed. 2004, 43, 5138;
60. b) H. Pellissier, Tetrahedron 2007, 63, 9267.
61. For a review on diarylprolinol ether catalyzed reactions, see: C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
62. Angew. Chem. Int. Ed. 2006, 45, 7876.