Diversity-oriented asymmetric catalysis (DOAC): Stereochemically divergent synthesis of thiochromanes using an imidazoline-aminophenol-nickel-catalyzed michael/henry reaction

Organic Letters

Volumn 16, Issue 6, 2014, Pages 1700-1703

  Arai, Takayoshi ^a   Yamamoto, Yushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINOPHENOL DERIVATIVE; CHROMAN DERIVATIVE; IMIDAZOLINE DERIVATIVE; NICKEL; SULFUR DERIVATIVE;

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

ALKENES; AMINOPHENOLS; CATALYSIS; CHROMANS; IMIDAZOLINES; MOLECULAR STRUCTURE; NICKEL; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 84896916712     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500361w     Document Type: Article

References (48)

1. Shen, H. C. Tetrahedron 2009, 65, 3931
2. Vilet, L. A. V.; Rodenhuis, N.; Dijkstra, D.; Wikström, H.; Pugsley, T. A.; Serpa, K. A.; Meltzer, L. T.; Heffner, T. G.; Wise, L. D.; Lajiness, M. E.; Huff, R. M.; Svensson, K.; Sundell, S.; Lundmmark, M. J. Med. Chem. 2000, 43, 2871
3. Chen, Y.; Zhang, Q.; Zhang, B.; Xia, P.; Xia, Y.; Yang, Z.-Y.; Kilgore, N.; Wild, C.; Morris-Natschke, S. L.; Lee, K.-H. Bioorg. Med. Chem. 2004, 12, 6383
4. Bolognesi, M. L.; Bortolini, M.; Cavalli, A.; Andrisano, V.; Rosini, M.; Minarini, A.; Melchiorre, C. J. J. Med. Chem. 2004, 47, 5945
5. Holland, H. L.; Manoharan, T. S.; Schweizer, F. Tetrahedron Lett. 1991, 5, 335
6. Sheppard, C. I.; Taylor, J. L.; Wiskur, S. L. Org. Lett. 2011, 13, 3794
7. Quallich, G. J.; Woodall, T. M. Tetrahedron Lett. 1993, 34, 785
8. Zeror, S.; Collin, J.; Fiaud, J.-C.; Zouioueche, A. Adv. Synth. Catal. 2008, 350, 197
9. Stepanenko, V.; Jesús, M. D.; Correa, W.; Bermúdez, L.; Vázquez, C.; Guzmán, I.; Ortiz-Marciales, M. Tetrahedron: Asymmetry 2009, 20, 2659
10. Manville, C. V.; Docherty, G.; Padda, R.; Wills, M. Eur. J. Org. Chem. 2011, 6893
11. Mercy, G.; Legay, R.; Lohier, J.-F.; Santos, J. S.-D. O.; Levillain, J.; Gaumont, A.-C.; Glea, M. Org. Biomol. Chem. 2010, 8, 2520
12. Dong, X.-Q.; Fang, X.; Wang, C.-J. Org. Lett. 2011, 13, 4426
13. Dong, X.-Q.; Fang, X.; Tao, H.-Y.; Zhou, X.; Wang, C.-J. Adv. Synth. Catal. 2012, 354, 1141
14. Zeng, X. Chem. Rev. 2013, 113, 6864
15. Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354
16. Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036
17. Dodda, R.; Goldman, J. J.; Mandel, T.; Zhao, C.-G.; Broker, G. A.; Tiekink, E. R. T. Adv. Synth. Catal. 2008, 350, 537
18. Rios, R.; Súnden, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8547
19. Rios, R.; Súnden, H.; Ibrahem, I.; Zhao, G.-L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8679
20. Zu, L.; Xie, H.; Li, H.; Wang, J.; Jiang, W.; Wang, W. Adv. Synth. Catal. 2007, 349, 1882
21. Dodda, R.; Mandel, T.; Zhao, C.-G. Tetrahedron Lett. 2008, 49, 1899
22. Zhao, G.-L.; Vesely, J.; Rios, R.; Ibrahem, I.; Súnden, H.; Córdova, A. Adv. Synth. Catal. 2008, 350, 237
23. Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177
24. Gao, Y.; Ren, Q.; Wu, H.; Li, M.; Wang, J. Chem. Commun. 2010, 46, 9232
25. Liu, T.-L.; He, Z.-L.; Wang, C.-J. Chem. Commun. 2011, 47, 9600
26. Du, Z.; Zhou, C.; Gao, Y.; Ren, Q.; Zhang, K.; Cheng, H.; Wang, W.; Wang, J. Org. Biomol. Chem. 2012, 10, 36
27. Choudhury, A. R.; Mukherjee, S. Adv. Synth. Catal. 2013, 355, 1989
28. Hayashi, Y.; Okano, T.; Aratake, S.; Hazelard, D. Angew. Chem., Int. Ed. 2007, 46, 4922
29. Tan, B.; Chua, P. J.; Li, Y.; Zhong, G. Org. Lett. 2008, 10, 2437
30. Varga, S.; Jakab, G.; Drahos, L.; Holczbauer, M.; Soós, T. Org. Lett. 2011, 13, 5416
31. Chintala, P.; Ghosh, S. K.; Long, E.; Headley, A. D.; Ni, B. Adv. Synth. Catal. 2011, 353, 2905
32. Singh, S.; Srivastava, A.; Samanta, S. Tetrahedron Lett. 2012, 53, 6087
33. Albertshofer, K.; Tan, B.; Barbas, C. F., III. Org. Lett. 2012, 14, 1834
34. Hou, W.; Zheng, B.; Chen, J.; Peng, Y. Org. Lett. 2012, 14, 2378
35. Shi, D.; Xie, Y.; Zhou, H.; Xia, C.; Huang, H. Angew. Chem., Int. Ed. 2012, 51, 1248
36. Raimondi, W.; Duque, M. M. S.; Goudedranche, S.; Quintard, A.; Constantieux, T.; Bugaut, X.; Bonne, D.; Rodriguez, J. Synthesis 2013, 45, 1659
37. Jaiswal, P. K.; Biswas, S.; Singh, S.; Pathak, B.; Mobin, S. M.; Samantha, S. RSC Adv. 2013, 3, 10644
38. Wu, L.; Wang, Y.; Song, H.; Tang, L.; Zhou, Z.; Tang, C. Adv. Synth. Catal. 2013, 355, 1053
39. Loh, C. C. J.; Hack, D.; Enders, D. Chem. Commun. 2013, 49, 10230
40. Loh, C. C. J.; Atodiresei, I.; Enders, D. Chem.-Eur. J. 2013, 19, 10822
41. Enders, D.; Hahn, R.; Atodiresei, I. Adv. Synth. Catal. 2013, 355, 1126
42. Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417
43. Arai, T.; Yokoyama, N.; Yanagisawa, A. Chem.-Eur. J. 2008, 14, 2052
44. Arai, T.; Yokoyama, N. Angew. Chem., Int. Ed. 2008, 47, 4989
45. Yokoyama, N.; Arai, T. Chem.Commun. 2009, 3285
46. Arai, T.; Yokoyama, N.; Mishiro, A.; Sato, H. Angew. Chem., Int. Ed. 2010, 49, 7895
47. Awata, A.; Arai, T. Chem.-Eur. J. 2012, 18, 8278
48. Awata, A.; Wasai, M.; Masu, H.; Kado, S.; Arai, T. Chem.-Eur. J. 2014, 20, 2470