N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines

Journal of the American Chemical Society

Volumn 136, Issue 4, 2014, Pages 1214-1217

  Wang, Ming ^a   Huang, Zhijian ^a   Xu, Jianfeng ^a   Chi, Yonggui Robin ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE; CHIRAL CENTERS; KINETIC RESOLUTION; N-HETEROCYCLIC; N-HETEROCYCLIC CARBENES; OPTICAL PURITY; REMOTE ACTIVATION;

CATALYSIS; NITROGEN COMPOUNDS;

ORGANIC COMPOUNDS;

AZOMETHINE IMINE; CARBENE; IMINE; N HETEROCYCLIC CARBENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; CYCLOADDITION; OPTICS;

AZO COMPOUNDS; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; IMINES; KINETICS; METHANE; MOLECULAR STRUCTURE; THIOSEMICARBAZONES;

EID: 84893465705     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja411110f     Document Type: Article

References (54)

1. Jungheim, L. N.; Sigmund, S. K. J. Org. Chem. 1987, 52, 4007-4013
2. Ternansky, R. J.; Holmes, R. A. Drugs Future 1990, 15, 149-157
3. Claramunt, R. M.; Elguero, J. Org. Prep. Proced. Int. 1991, 23, 273-320
4. Pezdirc, L.; Stanovnik, B.; Svete, J. Aust. J. Chem. 2009, 62, 1661-1666
5. Krueger, B.-W.; Fischer, R.; Bertram, H.-J.; Bretschneider, T.; Boehm, S.; Krebs, A.; Schenke, T.; Santel, H.-J.; Lurssen, K.; Schmidt, R. R.; Erdelen, C.; Wachendorff-Neumann, U.; Stendel, W. U.S. Patent 5,358,924.
6. Muehlebach, M.; Cederbaum, F.; Cornes, D.; Friedmann, A. A.; Glock, J.; Hall, G.; Indolese, A. F.; Kloer, D. P.; Goupil, G. L.; Maetzke, T.; Meier, H.; Schneider, R.; Stoller, A.; Szczepanski, H.; Wendeborna, S.; Widmer, H. Pest. Manag. Sci. 2011, 67, 1499-1521
7. Kamata, M.; Yamashita, T. Jpn. Kokai Tokkyo Koho, JP 2009196966.
8. Kamata, M.; Yamashita, T.; Kina, A.; Tawada, M.; Endo, S.; Mizukami, A.; Sasaki, M.; Tani, A.; Nakano, Y.; Watanabe, Y.; Furuyama, N.; Funami, M.; Amano, N.; Fukatsu, K. Bioorg. Med. Chem. Lett. 2012, 22, 4769-4772
9. Dorn, H.; Otto, A. Chem. Ber. 1968, 101, 3287-3301
10. Dorn, H.; Otto, A. Angew. Chem., Int. Ed. Engl. 1968, 7, 214-215
11. Shintani, R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 10778-10779
12. Suarez, A.; Downey, C. W.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11244-11245
13. Keller, M.; Sido, A. S. S.; Pale, P.; Sommer, J. Chem.-Eur. J. 2009, 15, 2810-2817
14. Yoshimura, K.; Oishi, T.; Yamaguchi, K.; Mizuno, N. Chem.-Eur. J. 2011, 17, 3827-3831
15. Imaizumi, T.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 20049-20052
16. Pezdirc, L.; Jovanovski, V.; Bevk, D.; Jakse, R.; Pirc, S.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron 2005, 61, 3977-3990
17. Suga, H.; Funyu, A.; Kakehi, A. Org. Lett. 2007, 9, 97-100
18. Sibi, M. P.; Rane, D.; Stanley, L. M.; Soeta, T. Org. Lett. 2008, 10, 2971-2974
19. Oishi, T.; Yoshimura, K.; Yamaguchi, K.; Mizuno, N. Chem. Lett. 2010, 39, 1086-1087
20. Li, J.; Lian, X.; Liu, X.; Lin, L.; Feng, X. M. Chem.-Eur. J. 2013, 19, 5134-5140
21. Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 6330-6331
22. Shapiro, N. D.; Shi, Y.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654-11655
23. Guo, H.; Liu, H.; Zhu, F. L.; Na, R.; Jiang, H.; Wu, Y.; Zhang, L.; Li, Z.; Yu, H.; Wang, B.; Xiao, Y.; Hu, X. P.; Wang, M. Angew. Chem., Int. Ed. 2013, 52, 12641-12645
24. Tong, M. C.; Chen, X.; Tao, H. Y.; Wang, C. J. Angew. Chem., Int. Ed. 2013, 52, 12377-12380
25. Qian, Y.; Zavalij, P. J.; Hu, W.; Doyle, M. P. Org. Lett. 2013, 15, 1564-1567
26. Xu, X.; Qian, Y.; Zavalij, P. Y.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 1244-1247
27. Chen, W.; Yuan, X.-H.; Li, R.; Du, W.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Adv. Synth. Catal. 2006, 348, 1818-1822
28. Chen, W.; Du, W.; Duan, Y.-Z.; Wu, Y.; Yang, S.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2007, 46, 7667-7670
29. Na, R. S.; Jing, C. F.; Xu, Q. H.; Jiang, H.; Wu, X.; Shi, J. Y.; Zhong, J. C.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W. A.; Guo, H.; Kwon, O. J. Am. Chem. Soc. 2011, 133, 13337-13348
30. Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334-5335
31. Zhu, G.; Sun, W.; Wu, C.; Li, G.; Hong, L.; Wang, R. Org. Lett. 2013, 15, 4988-4991
32. Shintani, R.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 12356-12357
33. Guo and co-workers reported elegant phosphine-catalyzed [4+3] reaction of related C,N-cyclic azomethine imines, see: Jing, C.; Na, R.; Wang, B.; Liu, H.; Zhang, L.; Liu, J.; Wang, M.; Zhong, J.; Kwon, O.; Guo, H. Adv. Synth. Catal. 2012, 354, 1023-1034
34. Lv, H.; Jia, W.-Q.; Sun, L.-H.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 8607-8610
35. Izquierdo, J.; Orue, A.; Scheidt, K. A. J. Am. Chem. Soc. 2013, 135, 10634-10637
36. Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810-8813
37. Chen, X.; Yang, S.; Song, B. A.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 11134-11137
38. Guin, J.; Sarkar, S. D.; Studer, A. Angew. Chem., Int. Ed. 2008, 47, 8727-8730
39. Knight, R. L.; Leeper, F. J. J. Chem. Soc,. Perkin Trans. 1 1998, 1891-1893
40. Sohn, S. S.; Bode, J. F. Org. Lett. 2005, 7, 3873-3876
41. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725-5728
42. He, M.; Struble, J. R.; Bode, J. F. J. Am. Chem. Soc. 2006, 128, 8418-8420
43. CCDC 968788 (3j) and CCDC 968789 (racemic 5q) contain 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.
44. Claramunt, R. M.; Elguero, J. Org. Prep. Proc. Int. 1991, 23, 273-320
45. Konaklieva, M. I.; Plotkin, B. J. Curr. Med. Chem.: Anti-Infect. Agents 2003, 2, 287-302
46. Schantl, J. G. Sci. Synth. 2004, 27, 731-824
47. Clavette, C.; Gan, W.; Bongers, A.; Markiewicz, T.; Toderian, A. B.; Gorelsky, S. I.; Beauchemin, A. M. J. Am. Chem. Soc. 2012, 134, 16111-16114
48. Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770-2771
49. Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347-1349
50. Shao, P. L.; Chen, X. Y.; Ye, S. Angew. Chem., Int. Ed. 2010, 49, 8412-8416
51. Cohen, D. T.; Eichman, C. C.; Phillips, E. M.; Zarefsky, E. R.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 7309-7313
52. Lu, S.; Poh, S. B.; Siau, W.-Y.; Zhao, Y. Angew. Chem., Int. Ed. 2013, 52, 1731-1734
53. Kuwano, S.; Harada, S.; Kang, B.; Oriez, R.; Yamaoka, Y.; Takasu, K.; Yamada, K. J. Am. Chem. Soc. 2013, 135, 11485-11488
54. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012-6042