Catalytic enantioselective halolactonization of enynes and Alkenes

Chemistry - A European Journal

Volumn 18, Issue 23, 2012, Pages 7296-7305

  Zhang, Wei ^a   Liu, Na ^a   Schienebeck, Casi M ^a   Decloux, Kyle ^a   Zheng, Suqing ^a   Werness, Jenny B ^a   Tang, Weiping ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

alkenes; allenes; enynes; halogens; halolactonization; organocatalysts

Indexed keywords

ALLENES; ENYNES; HALOGENS; HALOLACTONIZATION; ORGANOCATALYSTS;

CARBOXYLATION; CATALYSTS; ENANTIOSELECTIVITY; UREA;

OLEFINS;

ALKADIENE; ALKYNE; BROMINE; LACTONE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ALKADIENES; ALKYNES; BROMINE; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; LACTONES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84861581014     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103809     Document Type: Article

References (106)

1. K. E. Harding, T. H. Tiner, in Comprehensive Organic Synthesis, Vol.4 (Eds.:, B.M. Trost, I. Fleming,), Pergamon Press, Oxford, 1991, pp. 363
2. J. Rodriguez, J. P. Dulcere, Synthesis 1993, 1177
3. S. A. Snyder, D. S. Treitler, A. P. Brucks, Aldrichimica Acta 2011, 44, 27; for selected reviews on halogenated natural products, see
4. G. W. Gribble, Acc. Chem. Res. 1998, 31, 141
5. G. W. Gribble, J. Chem. Educ. 2004, 81, 1441
6. C. Paul, G. Pohnert, Nat. Prod. Rep. 2011, 28, 186; for selected recent total syntheses of halogenated natural products, see
7. G. M. Shibuya, J. S. Kanady, C. D. Vanderwal, J. Am. Chem. Soc. 2008, 130, 12514
8. C. Nilewski, R. W. Geisser, E. M. Carreira, Nature 2009, 457, 573
9. D. K. Bedke, G. M. Shibuya, A. Pereira, W. H. Gerwick, T. H. Haines, C. D. Vanderwal, J. Am. Chem. Soc. 2009, 131, 7570
10. C. Nilewski, R. W. Geisser, M. O. Ebert, E. M. Carreira, J. Am. Chem. Soc. 2009, 131, 15866
11. J. B. Werness, W. Tang, Org. Lett. 2011, 13, 3664, and references therein.
12. O. Kitagawa, T. Taguchi, Synlett 1999, 1191
13. H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147
14. G. Chen, S. Ma, Angew. Chem. 2010, 122, 8484
15. Angew. Chem. Int. Ed. 2010, 49, 8306
16. A. Castellanos, S. P. Fletcher, Chem. Eur. J. 2011, 17, 5766
17. C. K. Tan, L. Zhou, Y. Y. Yeung, Synlett 2011, 1335.
18. S. H. Kang, S. B. Lee, C. M. Park, J. Am. Chem. Soc. 2003, 125, 15748
19. S. H. Kang, C. M. Park, S. B. Lee, M. Kim, Synlett 2004, 1279
20. H. Y. Kwon, C. M. Park, S. B. Lee, J. H. Youn, S. H. Kang, Chem. Eur. J. 2008, 14, 1023.
21. A. Sakakura, A. Ukai, K. Ishihara, Nature 2007, 445, 900.
22. S. A. Snyder, Z. Y. Tang, R. Gupta, J. Am. Chem. Soc. 2009, 131, 5744.
23. K. C. Nicolaou, N. L. Simmons, Y. Ying, P. M. Heretsch, J. S. Chen, J. Am. Chem. Soc. 2011, 133, 8134.
24. J. L. Gustafson, D. Lim, S. J. Miller, Science 2010, 328, 1251.
25. M. D. Dowle, D. I. Davies, Chem. Soc. Rev. 1979, 8, 171
26. S. Ranganathan, K. M. Muraleedharan, N. K. Vaish, N. Jayaraman, Tetrahedron 2004, 60, 5273.
27. O. Kitagawa, T. Hanano, K. Tanabe, M. Shiro, T. Taguchi, J. Chem. Soc. Chem. Commun. 1992, 1005.
28. R. B. Grossman, R. J. Trupp, Can. J. Chem. 1998, 76, 1233
29. X. L. Cui, R. S. Brown, J. Org. Chem. 2000, 65, 5653
30. J. Haas, S. Piguel, T. Wirth, Org. Lett. 2002, 4, 297
31. M. Wang, L. Gao, W. Yue, W. Mai, Synth. Commun. 2004, 34, 1023
32. M. Wang, L. Gao, W. Mai, A. Xia, F. Wang, S. Zhang, J. Org. Chem. 2004, 69, 2874
33. J. Haas, S. Bissmire, T. Wirth, Chem. Eur. J. 2005, 11, 5777
34. J. M. Garnier, S. Robin, G. Rousseau, Eur. J. Org. Chem. 2007, 3281.
35. Z. Ning, R. Jin, J. Ding, L. Gao, Synlett 2009, 2291.
36. H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447
37. Angew. Chem. Int. Ed. Engl. 1996, 35, 448
38. G. Li, H. T. Chang, K. B. Sharpless, Angew. Chem. 1996, 108, 449
39. Angew. Chem. Int. Ed. Engl. 1996, 35, 451
40. E. N. Jacobsen, I. Marko, W. S. Mungall, G. Schroder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968.
41. D. C. Whitehead, R. Yousefi, A. Jaganathan, B. Borhan, J. Am. Chem. Soc. 2010, 132, 3298.
42. R. Yousefi, D. C. Whitehead, J. M. Mueller, R. J. Staples, B. Borhan, Org. Lett. 2011, 13, 608.
43. G. E. Veitch, E. N. Jacobsen, Angew. Chem. 2010, 122, 7490
44. Angew. Chem. Int. Ed. 2010, 49, 7332.
45. L. Zhou, C. K. Tan, X. Jiang, F. Chen, Y. Y. Yeung, J. Am. Chem. Soc. 2010, 132, 15474.
46. K. Murai, T. Matsushita, A. Nakamura, S. Fukushima, M. Shimura, H. Fujioka, Angew. Chem. 2010, 122, 9360
47. Angew. Chem. Int. Ed. 2010, 49, 9174.
48. C. K. Tan, L. Zhou, Y.-Y. Yeung, Org. Lett. 2011, 13, 2738.
49. Y. Cai, X. Liu, Y. Hui, J. Jiang, W. Wang, W. Chen, L. Lin, X. Feng, Angew. Chem. 2010, 122, 6296
50. Angew. Chem. Int. Ed. 2010, 49, 6160
51. Y. Cai, X. Liu, J. Jiang, W. Chen, L. Lin, X. Feng, J. Am. Chem. Soc. 2011, 133, 5636
52. Z.-M. Chen, Q.-W. Zhang, Z.-H. Chen, H. Li, Y.-Q. Tu, F.-M. Zhang, J.-M. Tian, J. Am. Chem. Soc. 2011, 133, 8818
53. L. Zhou, J. Chen, C. K. Tan, Y.-Y. Yeung, J. Am. Chem. Soc. 2011, 133, 9164
54. A. Jaganathan, A. Garzan, D. C. Whitehead, R. J. Staples, B. Borhan, Angew. Chem. 2011, 123, 2641
55. Angew. Chem. Int. Ed. 2011, 50, 2593
56. O. Lozano, G. Blessley, T. M. delCampo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur, Angew. Chem. 2011, 123, 8255
57. Angew. Chem. Int. Ed. 2011, 50, 8105
58. H. Li, F.-M. Zhang, Y.-Q. Tu, Q.-W. Zhang, Z.-M. Chen, Z.-H. Chen, J. Li, Chem. Sci. 2011, 2, 1839
59. U. Hennecke, C. H. Muller, R. Frohlich, Org. Lett. 2011, 13, 860
60. D. Huang, H. Wang, F. Xue, H. Guan, L. Li, X. Peng, Y. Shi, Org. Lett. 2011, 13, 6350
61. S. A. Snyder, D. S. Treitler, A. P. Brucks, J. Am. Soc. Chem. 2010, 132, 14303.
62. W. Zhang, H. Xu, H. Xu, W. Tang, J. Am. Chem. Soc. 2009, 131, 3832.
63. A. Hoffmann-Röder, N. Krause, Angew. Chem. 2004, 116, 1216
64. Angew. Chem. Int. Ed. 2004, 43, 1196
65. V. M. Dembitsky, T. Maoka, Prog. Lipid Res. 2007, 46, 328; for recent reviews on allene synthesis, see
66. K. M. Brummond, J. E. DeForrest, Synthesis 2007, 795
67. S. Yu, S. Ma, Chem. Commun. 2011, 47, 5384.
68. W. Zhang, S. Zheng, N. Liu, J. B. Werness, I. A. Guzei, W. Tang, J. Am. Chem. Soc. 2010, 132, 3664.
69. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289
70. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299
71. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
72. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
73. T. Akiyama, Chem. Rev. 2007, 107, 5744
74. X. H. Yu, W. Wang, Chem. Asian J. 2008, 3, 516
75. Z. G. Zhang, P. R. Schreiner, Chem. Soc. Rev. 2009, 38, 1187
76. S. J. Connon, Synlett 2009, 354.
77. B. Li, L. Jiang, M. Liu, Y. Chen, L. Ding, Y. Wu, Synlett 2005, 603
78. B. Vakulya, S. Varga, A. Csampai, T. Soos, Org. Lett. 2005, 7, 1967
79. S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525
80. Angew. Chem. Int. Ed. 2005, 44, 6367
81. J. X. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun. 2005, 4481; for other representative examples that use (thio)ureas 8a, 8e, or their analogues, see
82. J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048
83. J. Wang, H. Li, L. Zu, W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652
84. J. Lubkoll, H. Wennemers, Angew. Chem. 2007, 119, 6965
85. Angew. Chem. Int. Ed. 2007, 46, 6841
86. P. Dinér, M. Nielsen, S. Bertelsen, B. Niess, K. A. Jorgensen, Chem. Commun. 2007, 3646
87. M. Amere, M. C. Lasne, J. Rouden, Org. Lett. 2007, 9, 2621
88. D. R. Li, A. Murugan, J. R. Falck, J. Am. Chem. Soc. 2008, 130, 46
89. W. J. Nodes, D. R. Nutt, A. M. Chippindale, A. J. A. Cobb, J. Am. Chem. Soc. 2009, 131, 16016.
90. G. Lowe, Chem. Commun. 1965, 411.
91. Y. Zhang, K. Shibatomi, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 15038.
92. G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. S. Svendsen, I. Marko, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 8069
93. T. Bürgi, A. Baiker, J. Am. Chem. Soc. 1998, 120, 12920
94. P. Hammar, T. Marcelli, H. Hiemstra, F. Himo, Adv. Synth. Catal. 2007, 349, 2537
95. B. Tan, Y. Lu, X. Zeng, P. Chua, G. Zhong, Org. Lett. 2010, 12, 2682
96. H. Jiang, M. W. Paixao, D. Monge, K. A. Jorgensen, J. Am. Chem. Soc. 2010, 132, 2775.
97. T. Marcelli, R. N. S. vanderHaas, J. H. vanMaarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 943
98. Angew. Chem. Int. Ed. 2006, 45, 929.
99. K. Kacprzak, J. Gawronski, Synthesis 2001, 0961
100. S. K. Tian, Y. G. Chen, J. F. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621
101. T. Marcelli, J. H. vanMaarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 7658
102. Angew. Chem. Int. Ed. 2006, 45, 7496
103. S. J. Connon, Chem. Commun. 2008, 2499.
104. For a related trifunctional cinchona-derived thiourea catalyst that uses α-amino acids as linkers, see:, Q. Zhu, Y. Lu, Angew. Chem. 2010, 122, 7919
105. Angew. Chem. Int. Ed. 2010, 49, 7753.
106. For a discussion on the configurational stability of halonium ions, see:, S. E. Denmark, M. T. Burk, A. J. Hoover, J. Am. Chem. Soc. 2010, 132, 1232.