Asymmetric construction of functionalized bicyclic imides via [3 + 2] annulation of MBH carbonates catalyzed by dipeptide-based phosphines

Organic Letters

Volumn 14, Issue 14, 2012, Pages 3764-3767

  Zhong, Fangrui ^a   Chen, Guo Ying ^a   Han, Xiaoyu ^a   Yao, Weijun ^a   Lu, Yixin ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; DIPEPTIDE; IMIDE; MALEIMIDE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CARBONATES; DIPEPTIDES; IMIDES; MALEIMIDES; MOLECULAR STRUCTURE; PHOSPHINES; STEREOISOMERISM;

EID: 84864123232     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301647g     Document Type: Article

References (67)

1. Bush, J. A.; Long, B. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. J. Antibiot. 1987, 40, 668
2. Busby, D. J.; Copley, R. C. B.; Hueso, J. A.; Readshaw, S. A.; Rivera, A. J. Antibiot. 2000, 53, 670
3. Sondhi, S. M.; Rani, R.; Roy, P.; Agrawal, S. K.; Saxena, A. K. Bioorg. Med. Chem. Lett. 2009, 19, 1534
4. Stierle, A. A.; Stierle, D. B.; Patacini, B. J. Nat. Prod. 2008, 71, 856
5. Ding, G.; Jiang, L.; Guo, L.; Chen, X.; Zhang, H.; Che, Y. J. Nat. Prod. 2008, 71, 1861
6. Pacher, T.; Raninger, A.; Lorbeer, E.; Brecker, L.; But, P. P.-H.; Greger, H. J. Nat. Prod. 2010, 73, 1389
7. Ando, Y; Fuse, E; Figg, W. D. Clin. Cancer Res. 2002, 8, 1964
8. Berkovic, S. T. In The Treatment of Epilepsy; Wyllie, E., Ed.; Lea & Febiger: Philadelphia, 1993; p 547.
9. Crider, A. M.; Kolczynski, T. M.; Yates, K. M. J. Med. Chem. 1980, 23, 324
10. Fredenhagen, A.; Tamura, S. Y.; Kenny, P. T. M.; Komura, H.; Naya, Y.; Nakanishi, K.; Nishiyama, K.; Sugiura, M.; Kita, H. J. Am. Chem. Soc. 1987, 109, 4409
11. Sperry, J. Synthesis 2011, 3569
12. Muthaiah, S.; Hong, S. H. Synlett. 2011, 1481 and references therein
13. For an elegant review, see: Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650
14. Sasaki, M.; Kondo, Y.; Kawahata, M.; Yamaguchi, K.; Takeda, K. Angew. Chem., Int. Ed. 2011, 50, 6375
15. Wang, Y.; Liu, L.; Zhang, T.; Zhong, N.-J.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2012, 77, 4143
16. Zhao, Q.; Han, X.; Wei, Y.; Shi, M.; Lu, Y. Chem. Commun. 2012, 48, 970
17. Kwon, O.; Tamanoi, F.; Fiji, H.; Watanabe, M. PCT Int. Appl. WO 2010014054 A1 20100204, 2010.
18. Tamanoi, F.; Kwon, O.; Watanabe, M.; Fiji, H. PCT Int. Appl. WO 2007111948 A2 20071004, 2007.
19. Hansen, J. B.; Thomsen, M. S. PCT Int. Appl. WO 2012016569 A1 20120209, 2012.
20. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
21. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
22. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
23. Kwong, C. K.-W.; Fu, M. Y.; Lam, C. S.-L.; Toy, P. H. Synthesis 2008, 2307
24. Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102
25. Marinetti, A.; Voituriez, A. Synlett 2010, 174
26. Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724
27. Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836
28. Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426
29. Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988
30. Fang, Y. Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660
31. Voituriez, A.; Panossian, A.; Fleury-Brégeot, N.; Retailleau, P.; Marinetti, A. J. Am. Chem. Soc. 2008, 130, 14030
32. Sampath, M.; Loh, T.-P. Chem. Sci. 2010, 1, 739
33. Voituriez, A.; Pinto, N.; Neel, M.; Retailleau, P.; Marinetti, A. Chem.-Eur. J. 2010, 16, 12541
34. Xiao, H.; Chai, Z.; Zheng, C.-W.; Yang, Y.-Q.; Liu, W.; Zhang, J.-K.; Zhao, G. Angew. Chem., Int. Ed. 2010, 49, 4467
35. Pinto, N.; Retailleau, P.; Voituriez, A.; Marinetti, A. Chem. Commun. 2011, 1015-1017
36. Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293
37. Lin, M.; Kang, G.-Y.; Guo, Y.-A.; Yu, Z.-X. J. Am. Chem. Soc. 2012, 134, 398
38. Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470
39. Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643
40. Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Tetrahedron Lett. 2007, 48, 3617
41. Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.-Eur. J. 2008, 14, 4361
42. Wang, S.-X.; Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Synlett 2011, 2766
43. Xu, L.-W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807
44. Xu, L.-W.; Lu, Y. Org. Biomol. Chem. 2008, 6, 2047
45. Davie, E. A. C.; Mennen, S. M.; Xu, Y.; Miller, S. J. Chem. Rev. 2007, 107, 5759
46. Revell, J. D.; Wennemers, H. Curr. Opin. Chem. Biol. 2007, 11, 269
47. Berkessel, A. Curr. Opin. Chem. Biol. 2003, 7, 409
48. Miller, S. J. Acc. Chem. Res. 2004, 37, 601
49. Tsogoeva, S. B. Lett. Org. Chem. 2005, 2, 208
50. Han, X.; Wang, Y.; Zhong, F.; Lu, Y. Org. Biomol. Chem. 2011, 9, 6734
51. Zhong, F.; Wang, Y.; Han, X.; Huang, K.-W.; Lu, Y. Org. Lett. 2011, 13, 1310
52. Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726
53. Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2012, 51, 767
54. Han, X.; Wang, S.-X.; Zhong, F.; Lu, Y. Synthesis 2011, 1859
55. Zhao, Q.; Han, X.; Wei, Y.; Shi, M.; Lu., Y. Chem. Commun. 2012, 48, 970
56. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Chem. Sci. 2012, 3, 1231
57. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837
58. Zhong, F.; Luo, J.; Chen, G.-Y.; Dou, X.; Lu, Y. J. Am. Chem. Soc. 2012, 134, 10222
59. Tan, B.; Candeias, N. R.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 4672
60. Deng, H.-P.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2012, 354, 783
61. Peng, J.; Huang, X.; Jiang, L.; Cui, H.-L.; Chen, Y.-C. Org. Lett. 2011, 13, 4584
62. Liu, T.-Y.; Xie, M.; Chen, Y.-C. Chem. Soc. Rev. 2012, 41, 4101
63. Cheng, L.; Han, X.; Huang, H.; Wong, M. W.; Lu, Y. Chem. Commun. 2007, 4143
64. Cheng, L.; Wu, X.; Lu, Y. Org. Biomol. Chem. 2007, 5, 1018
65. Wu, X.; Jiang, Z.; Shen, H.-M.; Lu, Y. Adv. Synth. Catal. 2007, 349, 812
66. Zhu, Q.; Lu, Y. Chem. Commun. 2010, 46, 2235
67. Dou, X.; Han, X.; Lu, Y. Chem.-Eur. J. 2012, 18, 85; also see refs 11a-11i