Catalytic, asymmetric halofunctionalization of alkenes-a critical perspective

Angewandte Chemie - International Edition

Volumn 51, Issue 44, 2012, Pages 10938-10953

  Denmark, Scott E ^a   Kuester, William E ^a   Burk, Matthew T ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

alkenes; halogenation; homogeneous catalysis; Lewis base; synthetic methods

Indexed keywords

ASYMMETRIC INDUCTION; CRITICAL ANALYSIS; ENANTIOSELECTIVE; HOMOGENEOUS CATALYSIS; LEWIS BASE; NASCENT FIELD; SYNTHETIC METHODS;

CATALYSIS; HALOGENATION; OLEFINS; REACTION KINETICS;

ENANTIOSELECTIVITY;

ALKENE; HALOGEN; HALOGENATED HYDROCARBON;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; CYCLIZATION; HALOGENS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84867761321     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204347     Document Type: Review

References (106)

1. H. Gilman, Organic Chemistry: An Advanced Treatise, Vol. 1, Wiley, New York, 1938, pp. 36-43.
2. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca, 1953, pp. 658-670.
3. D. H. R. Barton, Experientia 1950, 6, 316-320
4. L. F. Fieser, M. Fieser, Steroids, Reinhold, New York, 1959, pp. 26-41.
5. In passing, it is interesting to note that dibromocholesterol was already reported in 1868!, J. Wislicenus, W. Moldenhauer, Justus Liebigs Ann. Chem. 1868, 146, 175-180.
6. A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354-362
7. P. A. Bartlett, in Asymmetric Synthesis, Vol. 3 (Ed.:, J. Morrison,), Academic Press, Orlando, 1983, pp. 411-454
8. P. A. Bartlett, D. P. Richardson, J. Myerson, Tetrahedron 1984, 40, 2317-2327.
9. A. Castellanos, S. P. Fletcher, Chem. Eur. J. 2011, 17, 5766-5776.
10. S. A. Snyder, D. S. Treitler, A. P. Brucks, Aldrichimica Acta 2011, 44, 27-40. Includes examples of racemic catalysis.
11. U. Hennecke, Chem. Asian J. 2012, 7, 456-465.
12. C. K. Tan, Z. Ling, Y.-Y. Yeung, Synlett 2011, 1335-1339.
13. C. W. Perkins, J. C. Martin, A. J. Arduengo, W. Lau, A. Alegria, J. K. Kochi, J. Am. Chem. Soc. 1980, 102, 7753-7759.
14. G. H. Schmid, D. G. Garratt, in The Chemistry of Double-Bonded Functional Groups, Part 2 (Ed.:, S. Patai,), Wiley, New York, 1977, pp. 725-912
15. G. H. Schmid, in The Chemistry of Double-Bonded Functional Groups, Vol. 2, Part 1 (Ed.:, S. Patai,), Wiley, New York, 1989, pp. 679-731.
16. D. Lenoir, C. Chiappe, Chem. Eur. J. 2003, 9, 1036-1044
17. G. Bellucci, C. Chiappe, R. Bianchini, D. Lenoir, R. Herges, J. Am. Chem. Soc. 1995, 117, 12001-12002.
18. I. Roberts, G. E. Kimball, J. Am. Chem. Soc. 1937, 59, 947-948.
19. G. A. Olah, J. M. Bollinger, J. Am. Chem. Soc. 1967, 89, 4744-4752
20. G. A. Olah, J. M. Bollinger, J. Am. Chem. Soc. 1968, 90, 947-953
21. G. A. Olah, J. M. Bollinger, J. Brinich, J. Am. Chem. Soc. 1968, 90, 2587-2594.
22. R. S. Brown, R. W. Nagorski, A. J. Bennet, R. E. D. McClung, G. H. M. Aarts, M. Klobukowski, R. McDonald, B. D. Santarsiero, J. Am. Chem. Soc. 1994, 116, 2448-2456
23. A. A. Neverov, R. S. Brown, J. Org. Chem. 1996, 61, 962-968
24. R. S. Brown, Acc. Chem. Res. 1997, 30, 131-137.
25. S. E. Denmark, M. T. Burk, A. J. Hoover, J. Am. Chem. Soc. 2010, 132, 1232-1233.
26. G. A. Olah, Q. Wang, G. Sandford, G. K. S. Prakash, J. Org. Chem. 1993, 58, 3194-3195
27. G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G. A. Olah, J. Am. Chem. Soc. 2004, 126, 15770-15776.
28. V. Gutmann, Coord. Chem. Rev. 1975, 15, 207-237
29. V. Gutmann, The Donor-Acceptor Approach to Molecular Interactions, Plenum, New York, 1978
30. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584-1663
31. Angew. Chem. Int. Ed. 2008, 47, 1560-1638.
32. R. B. Grossman, R. J. Trupp, Can. J. Chem. 1998, 76, 1233-1237.
33. X.-L. Cui, R. S. Brown, J. Org. Chem. 2000, 65, 5653-5658
34. R. S. Brown, A. A. Neverov, C. T. Liu, C. I. Maxwell, in In Recent Developments in Carbocation and Onium Ion Chemistry (Ed.:, K. Laali,), American Chemical Society, Washington, 2007, pp. 458-476.
35. J. Haas, S. Piguel, T. Wirth, Org. Lett. 2002, 4, 297-300
36. J. Haas, S. Bissmire, T. Wirth, Chem. Eur. J. 2005, 11, 5777-5785.
37. A. A. Neverov, R. S. Brown, J. Org. Chem. 1998, 63, 5977-5982.
38. This may not be true for nucleophiles stronger than olefins, however such reactions are beyond the scope of this review. See, A. A. Neverov, H. X. Feng, K. Hamilton, R. S. Brown, J. Org. Chem. 2003, 68, 3802-3810.
39. A. Sakakura, A. Ukai, K. Ishihara, Nature 2007, 445, 900-903.
40. A. R. Chamberlin, R. L. Mulholland, S. D. Kahn, W. J. Hehre, J. Am. Chem. Soc. 1987, 109, 672-677.
41. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
42. Angew. Chem. Int. Ed. 2006, 45, 1520-1543
43. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
44. Hydrogen Bonding in Organic Synthesis (Ed.:, P. M. Pihko,), Wiley-Interscience, Weinheim, 2009
45. M. Rueping, R. M. Koenigs, I. Atodiresei, Chem. Eur. J. 2010, 16, 9350-9365
46. M. Terada, Synthesis 2010, 1929-1982
47. M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, I. Atodiresei, Angew. Chem. 2011, 123, 6838-6853
48. Angew. Chem. Int. Ed. 2011, 50, 6706-6720
49. S. Schenker, A. Zamfir, M. Freund, S. B. Tsogoeva, Eur. J. Org. Chem. 2011, 2209-2222.
50. U. Hennecke, C. H. Müller, R. Fröhlich, Org. Lett. 2011, 13, 860-863.
51. S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590-7593
52. Angew. Chem. Int. Ed. 2005, 44, 7424-7427
53. G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31-39
54. M. Klussmann, L. Ratjen, S. Hoffmann, V. Wakchaure, R. Goddard, B. List, Synlett 2010, 2189-2192.
55. S. E. Denmark, M. T. Burk, Org. Lett. 2012, 14, 256-259.
56. D. Huang, H. Wang, F. Xue, H. Guan, L. Li, X. Peng, Y. Shi, Org. Lett. 2011, 13, 6350-6353.
57. R. Yousefi, D. C. Whitehead, J. M. Mueller, R. J. Staples, B. Borhan, Org. Lett. 2011, 13, 608-611.
58. G.-x. Li, Q.-q. Fu, X.-m. Zhang, J. Jiang, Z. Tang, Tetrahedron: Asymmetry 2012, 23, 245-251.
59. V. Rauniyar, A. D. Lackner, G. L. Hamilton, F. D. Toste, Science 2011, 334, 1681-1684.
60. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127
61. Angew. Chem. Int. Ed. 1998, 37, 2922-2959
62. D. R. Fenwick, H. B. Kagan, Top. Stereochem. 1999, 22, 257-296
63. T. Satyanarayana, S. Abraham, H. B. Kagan, Angew. Chem. 2009, 121, 464-503
64. Angew. Chem. Int. Ed. 2009, 48, 456-494.
65. G. E. Veitch, E. N. Jacobsen, Angew. Chem. 2010, 122, 7490-7493
66. Angew. Chem. Int. Ed. 2010, 49, 7332-7335.
67. K. Murai, T. Matsushita, A. Nakamura, S. Fukushima, M. Shimura, H. Fujioka, Angew. Chem. 2010, 122, 9360-9363
68. Angew. Chem. Int. Ed. 2010, 49, 9174-9177.
69. K. Murai, A. Nakamura, T. Matsushita, M. Shimura, H. Fujioka, Chem. Eur. J. 2012, 18, 8448-8453. This constitutes the only reported method for the enantioselective halofunctionalization of a tetrasubstituted alkene.
70. S. E. Denmark, M. T. Burk, Proc. Natl. Acad. Sci. USA 2010, 107, 20655-20660.
71. L. Zhou, C. K. Tan, X. Jiang, F. Chen, Y.-Y. Yeung, J. Am. Chem. Soc. 2010, 132, 15474-15476.
72. C. K. Tan, L. Zhou, Y.-Y. Yeung, Org. Lett. 2011, 13, 2738-2741.
73. C. K. Tan, C. Le, Y.-Y. Yeung, Chem. Commun. 2012, 48, 5793-5795.
74. J. Chen, L. Zhou, Y.-Y. Yeung, Org. Biomol. Chem. 2012, 10, 3808-3811.
75. J. Chen, L. Zhou, C. K. Tan, Y.-Y. Yeung, J. Org. Chem. 2012, 77, 999-1009.
76. W. Zhang, H. Xu, H. Xu, W. Tang, J. Am. Chem. Soc. 2009, 131, 3832-3833.
77. W. Zhang, S. Zheng, N. Liu, J. B. Werness, I. A. Guzei, W. Tang, J. Am. Chem. Soc. 2010, 132, 3664-3665.
78. W. Zhang, N. Liu, C. M. Schienebeck, K. Decloux, S. Zheng, J. B. Werness, W. Tang, Chem. Eur. J. 2012, 18, 7296-7305.
79. M. C. Dobish, J. N. Johnston, J. Am. Chem. Soc. 2012, 134, 6068-6071.
80. D. C. Whitehead, R. Yousefi, A. Jaganathan, B. Borhan, J. Am. Chem. Soc. 2010, 132, 3298-3300.
81. A. Jaganathan, A. Garzan, D. C. Whitehead, R. J. Staples, B. Borhan, Angew. Chem. 2011, 123, 2641-2644
82. Angew. Chem. Int. Ed. 2011, 50, 2593-2596.
83. K. C. Nicolaou, N. L. Simmons, Y. Ying, P. M. Heretsch, J. S. Chen, J. Am. Chem. Soc. 2011, 133, 8134-8137.
84. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547
85. E. J. Corey, M. C. Noe, J. Am. Chem. Soc. 1996, 118, 11038-11053.
86. O. Lozano, G. Blessley, T. Martinez del Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur, Angew. Chem. 2011, 123, 8255-8259
87. Angew. Chem. Int. Ed. 2011, 50, 8105-8109.
88. 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, 8818-8821.
89. H. Urabe, F Sato, in Lewis Acids in Organic Synthesis, Vol. 2 (Ed.:, H. Yamamoto,), Wiley-VCH, Weinheim, 2000, pp. 653-798.
90. K. Mikami, M. Terada, in Lewis Acids in Organic Synthesis, Vol. 2 (Ed.:, H. Yamamoto,), Wiley-VCH, Weinheim, 2000, pp. 799-848.
91. T. Inoue, O. Kitagawa, O. Ochiai, M. Shiro, T. Taguchi, Tetrahedron Lett. 1995, 36, 9333-9336.
92. T. Inoue, O. Kitagawa, A. Saito, T. Taguchi, J. Org. Chem. 1997, 62, 7384-7389.
93. O. Kitagawa, T. Hanano, K. Tanabe, M. Shiro, T. Taguchi, J. Chem. Soc. Chem. Commun. 1992, 1005-1007.
94. Y. Izumi, A. Tai, Stereo-Differentiating Reactions-The Nature of Asymmetric Reactions, Academic Press, New York, 1977, chapt. 2.
95. S. H. Kang, C. M. Park, S. B. Lee, M. Kim, Synlett 2004, 1279-1281.
96. S. H. Kang, S. B. Lee, C. M. Park, J. Am. Chem. Soc. 2003, 125, 15748-15749.
97. H. Y. Kwon, C. M. Park, S. B. Lee, J.-H. Youn, S. H. Kang, Chem. Eur. J. 2008, 14, 1023-1028.
98. Z. Ning, R. Jin, J. Ding, L. Gao, Synlett 2009, 2291-2294.
99. Y. Cai, X. Liu, Y. Hui, J. Jiang, W. Wang, W. Chen, L. Lin, X. Feng, Angew. Chem. 2010, 122, 6296-6300
100. Angew. Chem. Int. Ed. 2010, 49, 6160-6164
101. Y. Cai, X. Liu, J. Jiang, W. Chen, L. Lin, X. Feng, J. Am. Chem. Soc. 2011, 133, 5636-5639
102. Y. Cai, X. Liu, J. Li, W. Chen, W. Wang, L. Lin, X. Feng, Chem. Eur. J. 2011, 17, 14916-14921.
103. Y.-M. Wang, J. Wu, C. Hoong, V. Rauniyar, F. D. Toste, J. Am. Chem. Soc. 2012, 134, 12928-12931
104. X. Jiang, C. K. Tan, L. Zhou, Y.-Y. Yeung, Angew. Chem. 2012, 124, 7891-7895
105. Angew. Chem. Int. Ed. 2012, 51, 7771-7775
106. D. H. Paull, C. Fang, J. R. Donald, A. D. Pansick, S. F. Martin, J. Am. Chem. Soc. 2012, 134, 11128-11131.