Asymmetric direct vinylogous michael addition to 2-enoylpyridine N-oxides catalyzed by bifunctional thio-urea

Organic Letters

Volumn 16, Issue 21, 2014, Pages 5568-5571

  Rout, Subhrajit ^a   Ray, Sumit K ^b   Unhale, Rajshekhar A ^a   Singh, Vinod K ^a,b  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DICYANMETHANE; NITRILE; PYRIDINE DERIVATIVE; PYRIDINE N-OXIDE; THIOUREA;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; MOLECULAR STRUCTURE; NITRILES; PYRIDINES; STEREOISOMERISM; THIOUREA;

EID: 84910000343     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5025794     Document Type: Article

References (53)

1. Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; Müller, W. E. G.; Van Soest, R. W. M. J. Nat. Prod. 1996, 59, 1056-1060
2. Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. Tetrahedron Lett. 2000, 41, 9069-9073
3. Jayasinghe, L.; Jayasooriya, C. P.; Hara, N.; Fujimoto, Y. Tetrahedron Lett. 2003, 44, 8769-8771
4. Rao, K. V.; Kasanah, N.; Wahyuono, S.; Tekwani, B. L.; Schinazi, R. F.; Hamann, M. T. J. Nat. Prod. 2004, 67, 1314-1318
5. Morita, H.; Ishiuchi, K.; Haganuma, A.; Hoshino, T.; Obara, Y.; Nakahata, N.; Kobayashi, J. Tetrahedron 2005, 61, 1955-1960
6. Ishiuchi, K.; Kubato, T.; Mikami, Y.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioorg. Med. Chem. 2007, 15, 413-417
7. Ishuichi, K.; Kobota, T.; Ishiyama, H.; Hayashi, S.; Shibata, T.; Mori, K.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioorg. Med. Chem. 2011, 19, 749-753
8. Tang, Y.; Fu, Y.; Xiong, J.; Li, M.; Ma, G.-L.; Yang, G.-X.; Wei, B.-G.; Zhao, Y.; Zhang, H.-Y.; Hu, J.-F. J. Nat. Prod. 2013, 76, 1475-1484
9. González-Bello, C.; Castedo, L. Six-Membered Heterocycles: Pyridines in Modern Heterocyclic Chemistry; Alvarez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH: Weinheim, Germany, 2011; pp 1431-1525.
10. Henry, G. D. Tetrahedron 2004, 60, 6043-6061
11. Zhao, L.; Tsukano, C.; Kwon, E.; Takemoto, Y.; Hirama, M. Angew. Chem., Int. Ed. 2013, 52, 1722-1725
12. Tsukano, C.; Zhao, L.; Takemoto, Y.; Hirama, M. Eur. J. Org. Chem. 2010, 4198-4200
13. Malkov, A. V.; Kočovský Eur. J. Org. Chem. 2007, 29-36
14. Katritzky, A. R.; Lagowski, J. M. In Chemistry of the heterocyclic N-oxides; Academic Press: 1971.
15. Barroso, S.; Blay, G.; Pedro, J. R. Org. Lett. 2007, 9, 1983-1986
16. Barroso, S.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Org. Lett. 2011, 13, 402-405
17. Barroso, S.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2009, 351, 107-111
18. Livieri, A.; Boiocchi, M.; Desimoni, G.; Faita, G. Chem.-Eur. J. 2011, 17, 516-520
19. Singh, P. K.; Singh, V. K. Org. Lett. 2010, 12, 80-83
20. Singh, P. K.; Singh, V. K. Org. Lett. 2008, 10, 4121-4124
21. Ray, S. K.; Singh, P. K.; Singh, V. K. Org. Lett. 2011, 13, 5812-5815
22. George, J.; Reddy, B. V. S. Org. Biomol. Chem. 2012, 10, 4731-4738
23. Ray, S. K.; Singh, P. K.; Molleti, N.; Singh, V. K. J. Org. Chem. 2012, 77, 8802-8808
24. Ray, S. K.; Rout, S.; Singh, V. K. Org. Biomol. Chem. 2013, 11, 2412-2416
25. Rout, S.; Ray, S. K.; Singh, V. K. Org. Biomol. Chem. 2013, 11, 4537-4545
26. Livieri, A.; Boiocchi, M.; Desimoni, G.; Faita, G. Chem.-Eur. J. 2012, 18, 11662-11668
27. Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2014, 114, 6081-6129
28. Xue, D.; Chen, Y.-C.; Wang, Q.-W.; Cun, L.-F.; Zhu, J.; Deng, J.-G. Org. Lett. 2005, 7, 5293-5296
29. Poulsen, T. B.; Bell, M.; Jørgensen, K. A. Org. Biomol. Chem. 2006, 4, 63-70
30. Xie, J.-W.; Yue, L.; Xue, D.; Ma, X.-L.; Chen, Y. C.; Wu, Y.; Zhu, J.; Deng, J.-G. Chem. Commun. 2006, 1563-1565
31. Jiang, L.; Zheng, H.-T.; Liu, T.-Y.; Yue, L.; Chen, Y.-C. Tetrahedron 2007, 63, 5123-5128
32. Lu, J.; Liu, F.; Loh, T.-P. Adv. Synth. Catal. 2008, 350, 1781-1784
33. Lu, J.; Liu, F.; Zhao, W.-J.; Loh, T.-P. Tetarhedron Lett. 2008, 49, 5389-5392
34. Alemán, J.; Jacobsen, C. B.; Frisch, K.; Overgaard, j.; Jørgensen, K. A. Chem. Commun. 2008, 632-634
35. Lu, J.; Zhou, W.-J.; Liu, F.; Low, T.-P. Adv. Synth. Catal. 2008, 350, 1796-1800
36. Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 4479-4486
37. Schneider, C.; Abels, F. Org. Biomol. Chem. 2014, 12, 3531-3543
38. Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389-392
39. Liu, T.-Y.; Cui, H.-L.; Long, J.; Li, B.-J.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. J. Am. Chem. Soc. 2007, 129, 1878-1879
40. Song, C. E., Ed. Cinchona Alkaloids in Synthesis and Catalysis; Wiley-VCH: Weinheim, 2009.
41. Connon, S. J. Chem.-Eur. J. 2006, 12, 5418-5427
42. Connon, S. J. Chem. Commun. 2008, 2499-2510
43. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967-1969
44. Liu, T.-Y.; Long, J.; Li, B.-J.; Jiang, L.; Li, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem. 2006, 4, 2097-2099
45. Marcelli, T.; Van der Haas, R. N. S.; Van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929-931
46. Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhang, G.-C.; Xia, A.-B.; Xu, X.-S.; Xu, D.-Qi. Eur. J. Org. Chem. 2010, 4981-4985
47. de la Fuente Martin, G.; Mesía, L. R. Phytochemistry 1997, 46, 1087-1090
48. Feng, F.; Liu, J.-H.; Zhao, S.-X. Phytochemistry 1998, 49, 2557-2559
49. Shih, F.-Y.; Chen, T.-H.; Lu, M.-C.; Chen, W.-F.; Wen, Z.-H.; Kuo, Y.-H.; Sung, P.-J. Int. J. Mol. Sci. 2013, 14, 21781-21789
50. Li, J.-P.; Zhang, Y.-X.; Ji, Y. J. Chin. Chem. Soc. 2008, 55, 390-393
51. Schipper, D. J.; El-Salfiti, M.; Whipp, C. J.; Fagnou, K. Tetrahedron 2009, 65, 4977-4983
52. Namikoshi, M.; Nakata, H.; Yamada, H.; Nagai, M.; Saitoh, T. Chem. Pharm. Bull. 1987, 35, 2761-2773
53. Yang, B. O.; Ke, C.-Q.; He, Z.-S.; Yang, Y.-p.; Ye, Y. Tetrahedron Lett. 2002, 43, 1731-1733