Efficient and highly enantioselective construction of trifluoromethylated quaternary stereogenic centers via high-pressure mediated organocatalytic conjugate addition of nitromethane to β,β-disubstituted enones

Organic Letters

Volumn 16, Issue 22, 2014, Pages 5930-5933

  Kwiatkowski, Piotr ^a   Cholewiak, Agnieszka ^a   Kasztelan, Adrian ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84912535693     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502941d     Document Type: Article

References (64)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
2. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
3. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
4. Ojima, I. J. Org. Chem. 2013, 78, 6358
5. Theodoridis, G. In Agrochemicals, Archaeology, Green Chemistry & Water, Vol. 2; Tressaud, A., Ed.; Elsevier: 2006; Vol. 2, pp 121-175.
6. Pagliaro, M.; Ciriminna, R. J. Mater. Chem. 2005, 15, 4981
7. Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496
8. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455
9. Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119
10. Chem. Rev. 2008, 108, PR1-PR43.
11. Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633
12. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214
13. Zheng, Y.; Ma, J.-A. Adv. Synth. Catal. 2010, 352, 2745
14. Christoffers, J.; Baro, A., Eds. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Wiley-VCH: Weinheim, 2005.
15. Bella, M.; Gasperi, T. Synthesis 2009, 1583
16. Kimura, M.; Yamazaki, T.; Kitazume, T.; Kubota, T. Org. Lett. 2004, 6, 4651
17. Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625
18. Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769
19. El Qacemi, M.; Smits, H.; Cassayre, J. Y.; Mulholland, N. P.; Renold, P.; Godineau, E.; Pitterna, T. WO 2011/154555 A1, 2011.
20. Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959
21. Kawai, H.; Yuan, Z.; Kitayama, T.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2013, 52, 5575
22. Gao, J.-R.; Wu, H.; Xiang, B.; Yu, W.-B.; Han, L.; Jia, Y.-X. J. Am. Chem. Soc. 2013, 135, 2983
23. Chen, Q.; Wang, G.; Jiang, X.; Xu, Z.; Lin, L.; Wang, R. Org. Lett. 2014, 16, 1394
24. Ma, C.-H.; Kang, T.-R.; He, L.; Liu, Q.-Z. Eur. J. Org. Chem. 2014, 3981
25. Matoba, K.; Kawai, H.; Furukawa, T.; Kusuda, A.; Tokunaga, E.; Nakamura, S.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 5762
26. Kawai, H.; Okusu, S.; Yuan, Z.; Tokunaga, E.; Yamano, A.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2013, 52, 2221
27. Wu, S.; Pan, D.; Cao, C.; Wang, Q.; Chen, F.-X. Adv. Synth. Catal. 2013, 355, 1917
28. Su, Y.; Ling, J.-B.; Zhang, S.; Xu, P.-F. J. Org. Chem. 2013, 78, 11053
29. Liu, F.-L.; Chen, J.-R.; Feng, B.; Hu, X.-Q.; Ye, L.-H.; Lu, L.-Q.; Xiao, W.-J. Org. Biomol. Chem. 2014, 12, 1057
30. Chen, W.; Jing, Z.; Chin, K. F.; Qiao, B.; Zhao, Y.; Yan, L.; Tan, C.-H.; Jiang, Z. Adv. Synth. Catal. 2014, 356, 1292
31. Van Eldik, R.; Klaerner, F. G., Eds. High Pressure Chemistry: Synthetic Mechanistic and Supercritical Applications; Wiley-VCH: Weinheim, 2002.
32. Matsumoto, K.; Acheson, R. M., Eds. Organic Synthesis at High Pressure; Wiley: New York, 1991.
33. Jurczak, J.; Baranowski, B., Eds. High Pressure Chemical Synthesis; Elsevier: Amsterdam, 1989.
34. Zhang, Y.; Wang, W. Catal. Sci. Technol. 2012, 2, 42
35. Vicario, J.; Badía, D.; Carillo, L.; Reyes, E. Organocatalytic Enantioselective Conjugate Addition Reactions. A Powerful Tool for the Stereocontrolled Synthesis of Complex Molecules; RSC Publishing: Cambridge, 2010.
36. Roca-Lopez, D.; Sadaba, D.; Delso, I.; Herrera, R. P.; Tejero, T.; Merino, P. Tetrahedron: Asymmetry 2010, 21, 2561
37. Mitchell, C. E. T; Brenner, S. E.; Ley, S. V. Chem. Commun. 2005, 5346
38. Li, P.; Wang, Y.; Liang, X.; Ye, J. Chem. Commun. 2008, 3302
39. Kwiatkowski, P.; Dudziński, K.; Łyzwa, D. Org. Lett. 2011, 13, 3624
40. Akagawa, K.; Kudo, K. Angew. Chem., Int. Ed. 2012, 51, 12786
41. Hayashi, Y.; Kawamoto, Y.; Honda, M.; Okamura, D.; Umemiya, S.; Noguchi, Y.; Mukaiyama, T.; Sato, I. Chem.-Eur. J. 2014, 20, 12072
42. Mukaiyama, T.; Ogata, K.; Sato, I.; Hayashi, Y. Chem.-Eur. J. 2014, 20, 13583 and ref 7a, 7c
43. By analogy to the synthesis of (R)-baclofen: Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257
44. Siau, W.-Y.; Wang, J. Catal. Sci. Technol. 2011, 1, 1298
45. Connon, S. J. Chem. Commun. 2008, 2499
46. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967
47. Vakulya, B.; Varga, S.; Soós, T. J. Org. Chem. 2008, 73, 3475
48. Yang, W.; Du, D.-M. Org. Lett. 2010, 12, 5450
49. Matsumoto, K.; Uchida, T. Chem. Lett. 1981, 1673
50. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157
51. Łyzwa, D.; Dudziński, K.; Kwiatkowski, P. Org. Lett. 2012, 14, 1540
52. Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599
53. Sekiguchi, Y.; Sasaoka, A.; Shimomoto, A.; Fujioka, S.; Kotsuki, H. Synlett 2003, 1655
54. Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208
55. Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. Tetrahedron Lett. 2004, 45, 4353
56. Mori, K.; Yamauchi, T.; Maddaluno, J.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2011, 2080
57. Kwiatkowski, P.; Dudziński, K.; Łyzwa, D. Non-Classical Activation of Organocatalytic Reactions. In Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications; Dalko, P., Ed.; Wiley-VCH: Weinheim, 2013.
58. Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603
59. McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367
60. Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481
61. Malerich, J. P.; Hagihara, K.; Rawal, V. H. J. Am. Chem. Soc. 2008, 130, 14416
62. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672
63. Gajcy, K.; Lochyński, S.; Librowski, T. Curr. Med. Chem. 2010, 17, 2338
64. Preliminary results were presented by P.K. at the 18th European Symposium on Organic Chemistry in Marseille, 7-12 July, 2013.