Enantioselective organocatalyzed formal [4+2] cycloaddition of ketimines with allenoates: Easy access to a tetrahydropyridine framework with a chiral tetrasubstituted stereogenic carbon center

Asian Journal of Organic Chemistry

Volumn 3, Issue 4, 2014, Pages 412-415

  Takizawa, Shinobu ^a   Arteaga, Fernando Arteaga ^a   Yoshida, Yasushi ^a   Suzuki, Michitaka ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Allenoates; Ketimines; Organocatalysis; Tetrahydropyridines

Indexed keywords

EID: 84898930093     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201300244     Document Type: Article

References (61)

1. C. Y. Gan, T. Etoh, M. Hayashi, K. Komiyama, T. S. Kam, J. Nat. Prod. 2010, 73, 1107;
2. X. Y. Huang, A. Q. Zhang, D. L. Chen, Z. H. Jia, X. S. Li, Bioorg. Med. Chem. Lett. 2010, 20, 2859;
3. P. L. Katavic, D. A. Venables, P. I. Forster, G. Guymer, A. R. Carroll, J. Nat. Prod. 2006, 69, 1295;
4. D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435, and references therein.
5. H. Lin, Y. Tan, W. J. Liu, Z. C. Zhang, X. W. Sun, G. Q. Lin, Chem. Commun. 2013, 49, 4024;
6. J. D. Cuthbertson, R. J. K. Taylor, Angew. Chem. 2013, 125, 1530; Angew. Chem. Int. Ed. 2013, 52, 1490;
7. L. He, G. Laurent, P. Retailleau, B. Folléas, J. L. Brayer, G. Masson, Angew. Chem. 2013, 125, 11294; Angew. Chem. Int. Ed. 2013, 52, 11088;
8. S. Duttwyler, C. Lu, A. L. Rheingold, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2012, 134, 4064;
9. S. Takizawa, N. Inoue, H. Sasai, Tetrahedron Lett. 2011, 52, 377;
10. J. L. Leighton, A. K. Tambar, S. K. Lee, J. Am. Chem. Soc. 2010, 132, 10248;
11. X. Meng, Y. Huang, R. Chen, Chem. Eur. J. 2008, 14, 6852;
12. T. Kobayashi, M. Nakashima, T. Hakogi, K. Tanaka, S. Katsumura, Org. Lett. 2006, 8, 3809;
13. P. Somfai, A. S. Timen, A. Fischer, Chem. Commun. 2003, 1150.
14. H. Guo, Q. Xu, O. Kwon, J. Am. Chem. Soc. 2009, 131, 6318;
15. X. F. Xu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716.
16. For selected reviews and reports on the phosphine catalyzed [n+2] cycloadditons, see:
17. E. Li, Y. Huang, L. Liang, P. Xie, Org. Lett. 2013, 15, 3138;
18. H. Xiao, Z. Chai, R. S. Yao, G. Zhao, J. Org. Chem. 2013, 78, 9781;
19. Q.-Y. Zhao, Z. Lian, Y. Wei, M. Shi, Chem. Commun. 2012, 48, 1724;
20. S.-X. Wang, X. Han, F. Zhong, Y. Wang, Y. Lu, Synlett 2011, 2766;
21. A. Marinetti, A. Voituriez, Synlett 2010, 174;
22. M. Schuler, A. Voituriez, A. Marinetti, Tetrahedron: Asymmetry 2010, 21, 1569;
23. Z. Xu, X. Lu, J. Org. Chem. 1998, 63, 5031.
24. R. P. Wurz, G. Fu, J. Am. Chem. Soc. 2005, 127, 12234.
25. H. Xiao, Z. Chai, H. F. Wang, X. W. Wang, D. D. Cao, W. Liu, Y. P. Lu, Y. Q. Yang, G. Zhao, Chem. Eur. J. 2011, 17, 10562.
26. X. Y. Chen, R. C. Lin, S. Ye, Chem. Commun. 2012, 48, 1317;
27. X. Y. Chen, S. Ye, Eur. J. Org. Chem. 2012, 5723.
28. For recent reviews and reports on the enantioselective preparation of chiral tetrasubstituted carbon centers, see:
29. T. Yoshimura, T. Kinoshita, H. Yoshioka, T. Kawabata, Org. Lett. 2013, 15, 864;
30. S. Takizawa, E. Rémond, F. A. Arteaga, Y. Yoshida, V. Sridharan, J. Bayardon, S. Jugé, H. Sasai, Chem. Commun. 2013, 49, 8392;
31. H. Kawai, S. Okusu, Z. Yuan, E. Tokunaga, A. Yamano, M. Shiro, N. Shibata, Angew. Chem. 2013, 125, 2277; Angew. Chem. Int. Ed. 2013, 52, 2221;
32. Y. Yao, J. L. Li, Q. Q. Zhou, L. Dong, Y. C. Chen, Chem. Eur. J. 2013, 19, 9447;
33. F. L. Hu, Y. Wei, M. Shi, S. Pindi, G. Li, Org. Biomol. Chem. 2013, 11, 1921;
34. D. Wang, J. Liang, J. Feng, K. Wang, Q. Sun, L. Zhao, D. Li, W. Yan, R. Wang, Adv. Synth. Catal. 2013, 355, 548;
35. L. Yin, H. Takada, N. Kumagai, M. Shibasaki, Angew. Chem. 2013, 125, 7451; Angew. Chem. Int. Ed. 2013, 52, 7310;
36. L. Yin, Y. Otsuka, H. Takada, S. Mouri, R. Yazaki, N. Kumagai, M. Shibasaki, Org. Lett. 2013, 15, 698;
37. L.-H. Sun, Z.-Q. Liang, W.-Q. Jia, S. Ye, Angew. Chem. 2013, 125, 5915; Angew. Chem. Int. Ed. 2013, 52, 5803;
38. M. Hayashi, M. Sano, Y. Funahashi, S. Nakamura, Angew. Chem. 2013, 125, 5667; Angew. Chem. Int. Ed. 2013, 52, 5557;
39. D. Zhao, L. Mao, L. Wang, D. Yang, R. Wang, Chem. Commun. 2012, 48, 889;
40. J. Clayden, M. Donnard, J. Lefranc, D. J. Tetlow, Chem. Commun. 2011, 47, 4624;
41. Y. G. Wang, H. Mii, T. Kano, K. Maruoka, Bioorg. Med. Chem. Lett. 2009, 19, 3795;
42. M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853.
43. S. Takizawa, F. A. Arteaga, Y. Yoshida, M. Suzuki, H. Sasai, Org. Lett. 2013, 15, 4142.
44. S.-F. Zhu, T. Liu, S. Yang, S. Song, Q. L. Zhou, Tetrahedron 2012, 68, 7685;
45. W. Zhang, S.-F. Zhu, X.-C. Qiao, Q.-L. Zhou, Chem. Asian J. 2008, 3, 2105;
46. S.-F. Zhu, Y. Yang, L.-X. Wang, B. Liu, Q.-L. Zhou, Org. Lett. 2005, 7, 2333.
47. (R) or (S)-SITCP is commercially available from Sigma-Aldrich and Strem.
48. The groups of Fu, Zhou, and Shi independently used (S)-SITCP as a chiral nucleophilic organocatalyst, see:
49. R. J. Lundgren, A. Wilsily, N. Marion, C. Ma, Y. K. Chung, G. C. Fu, Angew. Chem. 2013, 125, 2585; Angew. Chem. Int. Ed. 2013, 52, 2525;
50. D. Wang, Y. Wei, M. Shi, Chem. Commun. 2012, 48, 2764;
51. Q.-G. Wang, S.-F. Zhu, L.-W. Ye, C.-Y. Zhou, X.-L. Sun, Y. Tang, Q.-L. Zhou, Adv. Synth. Catal. 2010, 352, 1914;
52. Y. K. Chung, G. C. Fu, Angew. Chem. 2009, 121, 2259; Angew. Chem. Int. Ed. 2009, 48, 2225.
53. S. Takizawa, N. Inoue, S. Hirata, H. Sasai, Angew. Chem. 2010, 122, 9919; Angew. Chem. Int. Ed. 2010, 49, 9725;
54. S. Takizawa, K. Matsui, H. Sasai, J. Synth. Org. Chem. Jpn. 2007, 65, 1089;
55. K. Matsui, S. Takizawa, H. Sasai, Synlett 2006, 761;
56. M. Shi, L.-H. Chen, C.-Q. Li, J. Am. Chem. Soc. 2005, 127, 3790;
57. M. Shi, L.-H. Chen, Chem. Commun. 2003, 1310.
58. The products 3a and 3a' were obtained in 88% total yield (3a:3a'=14.3:1) with 84% ee for 3a when using 10mol% catalyst loading.
59. An addition of Brønsted acid such as 2-naphthol (20mol%) led to a drastic drop of reaction rate and stereoselectivity; after 24h, 50% total yield of products 3a and 3a' (3a:3a'=1:1.2) were obtained in 19% ee for 3a and 11% ee for 3a', respectively.
60. CCDC964567 ((R)-3c) 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.
61. The absolute configuration of major products 3a-b and 3d-k were tentatively assigned to be the structures as shown in Scheme2 by comparison with an optical rotation of (-)-3c (91% ee, (R)), see the Supporting Information.