Catalytic asymmetric intermolecular bromoesterification of unfunctionalized olefins

Organic Letters

Volumn 16, Issue 14, 2014, Pages 3728-3731

  Li, Lijun ^a   Su, Cunxiang ^a   Liu, Xiaoqin ^a   Tian, Hua ^a   Shi, Yian ^a,b,c  

^a INSTITUTE OF CHEMISTRY   (China)

^b NANJING UNIVERSITY   (China)

^c Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84904546026     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501542r     Document Type: Article

References (70)

1. Li, G.; Kotti, S. R. S. S.; Timmons, C. Eur. J. Org. Chem. 2007, 2745
2. Rodríguez, F.; Fañanás, F. J. In Handbook of Cyclization Reactions; Ma, S., Ed; Wiley-VCH: New York, 2010; Vol. 4, pp 951-990.
3. Chen, G.; Ma, S. Angew. Chem., Int. Ed. 2010, 49, 8306
4. Castellanos, A.; Fletcher, S. P. Chem.-Eur. J. 2011, 17, 5766
5. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335
6. Hennecke, U. Chem.-Asian J. 2012, 7, 456
7. Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed. 2012, 51, 10938
8. Murai, K.; Fujioka, H. Heterocycles 2013, 87, 763
9. Tan, C. K.; Yeung, Y.-Y. Chem. Commum. 2013, 49, 7985
10. Chemler, S. R.; Bovino, M. T. ACS Catal. 2013, 3, 1076
11. Cheng, Y. A.; Yu, W. Z.; Yeung, Y.-Y. Org. Biomol. Chem. 2014, 12, 2333
12. Sakakura, A.; Ukai, A.; Ishihara, K. Nature 2007, 445, 900
13. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298
14. Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664
15. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
16. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew. Chem., Int. Ed. 2010, 49, 9174
17. Hennecke, U.; Müller, C. H.; Fröhlich, R. Org. Lett. 2011, 13, 860
18. Chen, Z.-M.; Zhang, Q.-W.; Chen, Z.-H.; Li, H.; Tu, Y.-Q.; Zhang, F.-M.; Tian, J.-M. J. Am. Chem. Soc. 2011, 133, 8818
19. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164
20. Lozano, O.; Blessley, G.; Campo, T. M. d.; Thompson, A. L.; Giuffredi, G. T.; Bettati, M.; Walker, M.; Borman, R.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 8105
21. Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681
22. Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 6068
23. Paull, D. H.; Fang, C.; Donald, J. R.; Pansick, A. D.; Martin, S. F. J. Am. Chem. Soc. 2012, 134, 11128
24. Wang, Y.-M.; Wu, J.; Hoong, C.; Rauniyar, V.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 12928
25. Ikeuchi, K.; Ido, S.; Yoshimura, S.; Asakawa, T.; Inai, M.; Hamashima, Y.; Kan, T. Org. Lett. 2012, 14, 6016
26. Tungen, J. E.; Nolsøe, J. M. J.; Hansen, T. V. Org. Lett. 2012, 14, 5884
27. Denmark, S. E.; Burk, M. T. Org. Lett. 2012, 14, 256
28. Chen, F.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2013, 135, 1232
29. Wilking, M.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Hennecke, U. J. Am. Chem. Soc. 2013, 135, 8133
30. Tripathi, C. B.; Mukherjee, S. Angew. Chem., Int. Ed. 2013, 52, 8450
31. Zhao, Y.; Jiang, X.; Yeung, Y.-Y. Angew. Chem., Int. Ed. 2013, 52, 8597
32. Romanov-Michailidis, F.; Guénée, L.; Alexakis, A. Angew. Chem., Int. Ed. 2013, 52, 9266
33. Sawamura, Y.; Nakatsuji, H.; Sakakura, A.; Ishihara, K. Chem. Sci. 2013, 4, 4181
34. Yin, Q.; You, S.-L. Org. Lett. 2013, 15, 4266
35. Yousefi, R.; Ashtekar, K. D.; Whitehead, D. C.; Jackson, J. E.; Borhan, B. J. Am. Chem. Soc. 2013, 135, 14524
36. Jaganathan, A.; Staples, R. J.; Borhan, B. J. Am. Chem. Soc. 2013, 135, 14806
37. Xie, W.; Jiang, G.; Liu, H.; Hu, J.; Pan, X.; Zhang, H.; Wan, X.; Lai, Y.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 12924
38. Zeng, X.; Miao, C.; Wang, S.; Xia, C.; Sun, W. Chem. Commun. 2013, 49, 2418
39. Liu, H.; Jiang, G.; Pan, X.; Wan, X.; Lai, Y.; Ma, D.; Xie, W. Org. Lett. 2014, 16, 1908
40. Yin, Q.; You, S.-L. Org. Lett. 2014, 16, 1810
41. Ke, Z.; Tan, C. K.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2014, 136, 5627
42. For a leading review of asymmetric intermolecular halogenation of olefins, see: Chen, J.; Zhou, L. Synthesis 2014, 586
43. Cai, Y.; Liu, X.; Hui, Y.; Jiang, J.; Wang, W.; Chen, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2010, 49, 6160
44. Cai, Y.; Liu, X.; Jiang, J.; Chen, W.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2011, 133, 5636
45. Cai, Y.; Liu, X.; Li, J.; Chen, W.; Wang, W.; Lin, L.; Feng, X. Chem.-Eur. J. 2011, 17, 14916
46. Cai, Y.; Liu, X.; Zhou, P.; Kuang, Y.; Lin, L.; Feng, X. Chem. Commun. 2013, 49, 8054
47. Nicolaou, K. C.; Simmons, N. L.; Ying, Y.; Heretsch, P. M.; Chen, J. S. J. Am. Chem. Soc. 2011, 133, 8134
48. Hu, D. X.; Shibuya, G. M.; Burns, N. Z. J. Am. Chem. Soc. 2013, 135, 12960
49. Alix, A.; Lalli, C.; Retailleau, P.; Masson, G. J. Am. Chem. Soc. 2012, 134, 10389
50. Honjo, T.; Phipps, R. J.; Rauniyar, V.; Toste, F. D. Angew. Chem., Int. Ed. 2012, 51, 9684
51. Zhang, W.; Liu, N.; Schienebeck, C. M.; Zhou, X.; Izhar, I. I.; Guzei, I. A.; Tang, W. Chem. Sci. 2013, 4, 2652
52. Zhang, Y.; Xing, H.; Xie, W.; Wan, X.; Lai, Y.; Ma, D. Adv. Synth. Catal. 2013, 355, 68
53. El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790
54. El-Qisairi, A. K.; Qaseer, H. A.; Katsigras, G.; Lorenzi, P.; Trivedi, U.; Tracz, S.; Hartman, A.; Miller, J. A.; Henry, P. M. Org. Lett. 2003, 5, 439
55. 4- l -DIPT-catalyzed asymmetric chlorohydrin of unfunctionalized olefins, see: Sakurada, I.; Yamasaki, S.; Göttlich, R.; Iida, T.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 1245
56. For Mn(Salen)-catalyzed asymmetric chlorination of unfunctionalized olefins, see: Adam, W.; Mock-Knoblauch, C.; Saha-Möller, C. R.; Herderich, M. J. Am. Chem. Soc. 2000, 122, 9685
57. Li, G.-X.; Fu, Q.-Q.; Zhang, X.-M.; Jiang, J.; Tang, Z. Tetrahedron: Asymmetry 2012, 23, 245
58. Huang, D.; Wang, H.; Xue, F.; Guan, H.; Li, L.; Peng, X.; Shi, Y. Org. Lett. 2011, 13, 6350
59. Huang, D.; Liu, X.; Li, L.; Cai, Y.; Liu, W.; Shi, Y. J. Am. Chem. Soc. 2013, 135, 8101
60. Guan, H.; Wang, H.; Huang, D.; Shi, Y. Tetrahedron 2012, 68, 2728
61. Li, L.; Li, Z.; Huang, D.; Wang, H.; Shi, Y. RSC Adv. 2013, 3, 4523
62. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157
63. Jaganathan, A.; Garzan, A.; Whitehead, D. C.; Staples, R. J.; Borhan, B. Angew. Chem., Int. Ed. 2011, 50, 2593
64. Yousefi, R.; Whitehead, D. C.; Mueller, J. M.; Staples, R. J.; Borhan, B. Org. Lett. 2011, 13, 608
65. Li, H.; Zhang, F.-M.; Tu, Y.-Q.; Zhang, Q.-W.; Chen, Z.-M.; Chen, Z.-H.; Li, J. Chem. Sci. 2011, 2, 1839
66. Müller, C. H.; Wilking, M.; Rühlmann, A.; Wibbeling, B.; Hennecke, U. Synlett 2011, 2043
67. Also see ref 3b,3g,3i,3n,3r,3w-3y,3ac.
68. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768
69. Kasai, M.; Kawai, K.-i.; Imuta, M.; Ziffer, H. J. Org. Chem. 1984, 49, 675
70. Wei, S.; Messerer, R.; Tsogoeva, S. B. Chem.-Eur. J. 2011, 17, 14380