Organocatalytic cascade sulfa-Michael/aldol reaction of β,β-disubstituted enones: Enantioselective synthesis of tetrahydrothiophenes with a trifluoromethylated quaternary center

Journal of Organic Chemistry

Volumn 78, Issue 21, 2013, Pages 11053-11058

  Su, Yu ^a   Ling, Jun Bing ^a   Zhang, Shuang ^a   Xu, Peng Fei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE REACTIONS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED; HIGH ENANTIOSELECTIVITY; ORGANOCATALYTIC; QUATERNARY CARBON; QUATERNARY CENTERS; STEREOCENTERS;

ADDITION REACTIONS; SELECTIVE CATALYTIC REDUCTION;

ENANTIOSELECTIVITY;

CHALCONE DERIVATIVE; THIOPHENE DERIVATIVE;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; ENANTIOSELECTIVITY; FLUORINE NUCLEAR MAGNETIC RESONANCE; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84887083597     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4016024     Document Type: Article

References (50)

1. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
2. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
3. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004.
4. Uneyama, K. Organofluorine Chemistry; Blackwell Publishing Ltd.: Oxford, 2006.
5. Ma, J. A.; Cahard, D. Chem. Rev. 2008, 108, PR1
6. Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214
7. Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804
8. Lectard, S.; Hamashima, Y.; Sodeoka, M. Adv. Synth. Catal. 2010, 352, 2708
9. Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J. F. Chem. Soc. Rev. 2011, 40, 2867
10. Nie, J.; Guo, H. C.; Cahard, D.; Ma, J. A. Chem. Rev. 2011, 111, 455
11. Xie, H.; Zhang, Y.; Zhang, S.; Chen, X.; Wang, W. Angew. Chem., Int. Ed. 2011, 50, 11773
12. Liu, Y. L.; Shi, T. D.; Zhou, F.; Zhao, X. L.; Wang, X.; Zhou, J. Org. Lett. 2011, 13, 3826
13. Palacio, C.; Connon, S. J. Org. Lett. 2011, 13, 1298
14. Matoba, K.; Kawai, H.; Furukawa, T.; Kusuda, A.; Tokunaga, E.; Nakamura, S.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 5762
15. Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959
16. Kawai, H.; Okusu, S.; Yuan, Z.; Tokunaga, E.; Yamano, A.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2013, 52, 2221
17. Kawai, H.; Yuan, Z.; Kitayama, T.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2013, 52, 5575
18. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
19. Yu, X.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037
20. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
21. Mayano, A.; Rios, R. Chem. Rev. 2011, 111, 4703
22. Mo, J.; Chen, X.; Chi, Y.R. J. Am. Chem. Soc. 2012, 134, 8810
23. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
24. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363
25. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969
26. Bella, M.; Gasperi, T. Synthesis 2009, 1583
27. Lu, H. H.; Zhang, F. G.; Meng, X. G.; Duan, S. W.; Xiao, W. J. Org. Lett. 2009, 11, 3946
28. Wen, S.; Li, P.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun. 2010, 46, 4806
29. Kwiatkowski, P.; Dudziński, K.; Łyzwa, D. Org. Lett. 2011, 13, 3624
30. Jia, Z. X.; Luo, Y. C.; Wang, Y.; Chen, L.; Xu, P. F. Chem.-Eur. J. 2012, 18, 12958
31. Ling, J. B.; Wang, W. P.; Xu, P. F. CatChemCat 2011, 3, 302
32. Ling, J. B.; Su, Y.; Zhu, H. L.; Wang, G. Y.; Xu, P. F. Org. Lett. 2012, 14, 1090
33. Duan, G. J.; Ling, J. B.; Wang, W. P.; Luo, Y. C.; Xu, P. F. Chem. Commun. 2013, 49, 4625
34. Tian, L.; Hu, X. Q.; Li, Y. H.; Xu, P. F. Chem. Commun. 2013, 49, 7213
35. Storer, R. L.; Aciro, C.; Jones, L. H. Chem. Soc. Rev. 2011, 40, 2330
36. Alemán, J.; Parra, A.; Jiang, H.; Jørgensen, K. A. Chem.-Eur. J. 2011, 17, 6890
37. Malerich, J. P.; Hagihara, K.; Rawal, V. H. J. Am. Chem. Soc. 2008, 130, 14416
38. Zhu, Y.; Malerich, J. P.; Rawal, V. H. Angew. Chem., Int. Ed. 2010, 49, 153
39. Dai, L.; Wang, S. X.; Chem, F. E. Adv. Synth. Catal. 2010, 352, 2137
40. Yang, W.; Du, D. M. Chem. Commun. 2011, 47, 12706
41. O'Connor, C. J.; Roydhouse, M. D.; Przybył, A. M.; Wall, M. D.; Southern, J. M. J. Org. Chem. 2010, 75, 2534
42. Tang, J.; Xu, D. Q.; Xia, A. B.; Wang, Y. F.; Jiang, J. R.; Luo, S. P.; Xu, Z. Y. Adv. Synth. Catal. 2010, 352, 2121
43. Duan, S. W.; Li, Y.; Liu, Y. Y.; Zou, Y. Q.; Shi, D. Q.; Xiao, W. J. Chem. Commun. 2012, 48, 5160
44. Williams, D. R.; Jass, P. A.; Tse, H. L. A.; Gaston, R. D. J. Am. Chem. Soc. 1990, 112, 4552
45. Li, A. H.; Dai, L. X.; Hou, X.-L.; Huang, Y. Z.; Li, F. W. J. Org. Chem. 1996, 61, 489
46. Julienne, K.; Metzner, P. J. Org. Chem. 1998, 63, 4532
47. Zanardi, J.; Lamazure, D.; Miniere, S.; Reboul, V.; Metzner, P. J. Org. Chem. 2002, 67, 9083
48. Piccinini, A.; Kavanagh, S. A.; Connon, P. B.; Connon, S. J. Org. Lett. 2010, 12, 608
49. CCDC 933238 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
50. Konno, T.; Takehana, T.; Mishima, M.; Ishihara, T. J. Org. Chem. 2006, 71, 3545