Stereoselective rearrangements with chiral hypervalent iodine reagents

Angewandte Chemie - International Edition

Volumn 52, Issue 27, 2013, Pages 7018-7022

  Farid, Umar ^a   Malmedy, Florence ^a   Claveau, Romain ^a   Albers, Lena ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

acetals; aryl migration; hypervalent iodine; rearrangement; stereoselective synthesis

Indexed keywords

ACETALS; ARYL MIGRATION; HYPERVALENT IODINE; REARRANGEMENT; STEREOSELECTIVE SYNTHESIS;

IODINE COMPOUNDS; KETONES; STEREOCHEMISTRY; STEREOSELECTIVITY;

IODINE;

EID: 84879354137     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302358     Document Type: Article

References (96)

1. T. Wirth, Angew. Chem. 2001, 113, 2893-2895
2. Angew. Chem. Int. Ed. 2001, 40, 2812-2814
3. T. Wirth, in Organic Synthesis Highlights V (Eds.:, H.-G. Schmalz, T. Wirth,), Wiley-VCH, Weinheim, 2003, pp. 144-150
4. T. Wirth, Top. Curr. Chem. 2003, 224
5. T. Wirth, Angew. Chem. 2005, 117, 3722-3731
6. Angew. Chem. Int. Ed. 2005, 44, 3656-3665
7. R. M. Moriarty, J. Org. Chem. 2005, 70, 2893-2903
8. U. Ladziata, V. V. Zhdankin, Synlett 2007, 527-537
9. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299-5358
10. E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214-9234
11. Angew. Chem. Int. Ed. 2009, 48, 9052-9070
12. F. V. Singh, T. Wirth, Comprehensive Organic Chemistry II (Ed.: P. Knochel), Elsevier, 2013, in press.
13. H. Tohma, Y. Kita, Adv. Synth. Catal. 2004, 346, 111-124
14. M. Uyanik, K. Ishihara, Chem. Commun. 2009, 2086-2099.
15. M. Ngatimin, D. W. Lupton, Aust. J. Chem. 2010, 63, 653-658
16. H. Liang, M. A. Ciufolini, Angew. Chem. 2011, 123, 12051-12053
17. Angew. Chem. Int. Ed. 2011, 50, 11849-11851
18. U. Farid, T. Wirth, Asymmetric Synthesis II (Eds.:, M. Christmann, S. Bräse,), Wiley VCH, 2012, pp. 197-203
19. M. Brown, U. Farid, T. Wirth, Synlett 2013, 24, 424-431.
20. T. Imamoto, H. Koto, Chem. Lett. 1986, 15, 967-968
21. D. G. Ray III, G. F. Koser, J. Am. Chem. Soc. 1990, 112, 5672-5673
22. D. G. Ray III, G. F. Koser, J. Org. Chem. 1992, 57, 1607-1610
23. H. Tohma, S. Takizawa, H. Watanabe, Y. Fukuoka, T. Maegawa, Y. Kita, J. Org. Chem. 1999, 64, 3519-3523
24. V. V. Zhdankin, J. T. Smart, P. Zhao, P. Kiprof, Tetrahedron Lett. 2000, 41, 5299-5302.
25. E. Hatzigrigoriou, A. Varvoglis, M. Bakola-Christianopoulou, J. Org. Chem. 1990, 55, 315-318
26. R. D. Richardson, T. K. Page, S. Altermann, S. M. Paradine, A. N. French, T. Wirth, Synlett 2007, 538-542
27. S. M. Altermann, R. D. Richardson, T. K. Page, R. K. Schmidt, E. Holland, U. Mohammed, S. M. Paradine, A. N. French, C. Richter, A. M. Bahar, B. Witulski, T. Wirth, Eur. J. Org. Chem. 2008, 5315-5328
28. U. Farooq, S. Schäfer, A. A. Shah, D. M. Freudendahl, T. Wirth, Synthesis 2010, 1023-1029.
29. M. Ochiai, Y. Kitagawa, N. Takayama, Y. Takaoka, M. Shiro, J. Am. Chem. Soc. 1999, 121, 9233-9234.
30. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. 2008, 120, 3847-3850
31. Angew. Chem. Int. Ed. 2008, 47, 3787-3790
32. S. Quideau, G. Lyvinec, M. Marguerit, K. Bathany, A. Ozanne-Beaudenon, T. Buffeteau, D. Cavagnat, A. Chénedé, Angew. Chem. 2009, 121, 4675-4679
33. Angew. Chem. Int. Ed. 2009, 48, 4605-4609
34. J. K. Boppisetti, V. B. Birman, Org. Lett. 2009, 11, 1221-1223
35. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. 2010, 122, 2221-2223
36. Angew. Chem. Int. Ed. 2010, 49, 2175-2177
37. A. V. Kelly, A. M. Harned, Chem. Commun. 2013, 49, 3001-3003
38. T. Dohi, N. Takenaga, T. Nakae, Y. Toyoda, M. Yamasaki, M. Shiro, H. Fujioka, A. Maruyama, Y. Kita, J. Am. Chem. Soc. 2013, 135, 4558-4566.
39. T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26
40. U. H. Hirt, B. Spingler, T. Wirth, J. Org. Chem. 1998, 63, 7674-7679
41. U. H. Hirt, M. F. H. Schuster, A. N. French, O. G. Wiest, T. Wirth, Eur. J. Org. Chem. 2001, 1569-1579
42. A. C. Boye, D. Meyer, C. K. Ingison, A. N. French, T. Wirth, Org. Lett. 2003, 5, 2157-2159
43. A. Y. Koposov, V. V. Boyarskikh, V. V. Zhdankin, Org. Lett. 2004, 6, 3613-2615
44. M. Fujita, S. Okuno, H. J. Lee, T. Sugimura, T. Okuyama, Tetrahedron Lett. 2007, 48, 8691-8694
45. M. Fujita, Y. Ookubo, T. Sugimura, Tetrahedron Lett. 2009, 50, 1298-1300
46. M. Fujita, Y. Yoshida, K. Miyata, A. Wakisaka, T. Sugimura, Angew. Chem. 2010, 122, 7222-7225
47. Angew. Chem. Int. Ed. 2010, 49, 7068-7071.
48. C. Röben, J. A. Souto, Y. González, A. Lishchynskyi, K. Muñiz, Angew. Chem. 2011, 123, 9650-9654
49. Angew. Chem. Int. Ed. 2011, 50, 9478-9482
50. C. Röben, J. A. Souto, E. C. Escudero-Adán, K. Muñiz, Org. Lett. 2013, 15, 1008-1011.
51. U. Farid, T. Wirth, Angew. Chem. 2012, 124, 3518-3522
52. Angew. Chem. Int. Ed. 2012, 51, 3462-3465.
53. W. Kong, P. Feige, T. de Haro, C. Nevado, Angew. Chem. 2013, 125, 2529-2533
54. Angew. Chem. Int. Ed. 2013, 52, 2469-2473.
55. T. Wirth, Top. Curr. Chem. 2003, 224, 185-208
56. M. W. Justik, G. F. Koser, Tetrahedron Lett. 2004, 45, 6159-6163
57. L. F. Silva, Molecules 2006, 11, 421-434
58. J. M. Vatèle, Synlett 2008, 1785-1788
59. A. A. Zagulyaeva, C. T. Banek, M. S. Yusubov, V. V. Zhdankin, Org. Lett. 2010, 12, 4644-4647
60. M.-A. Beaulieu, C. Sabot, N. Achache, K. C. Guérard, S. Canesi, Chem. Eur. J. 2010, 16, 11224-11228
61. M.-A. Beaulieu, K. C. Guérard, G. Maertens, C. Sabot, S. Canesi, J. Org. Chem. 2011, 76, 9460-9471
62. G. Jacquemot, S. Canesi, J. Org. Chem. 2012, 77, 7588-7594.
63. M. W. Justik, G. F. Koser, Molecules 2005, 10, 217-225
64. L. F. Silva, Jr., R. S. Vasconcelos, M. A. Nogueira, Org. Lett. 2008, 10, 1017-1020.
65. L. F. Silva, Jr., F. A. Siqueira, E. C. Pedrozo, F. Y. M. Vieira, A. C. Doriguetto, Org. Lett. 2007, 9, 1433-1436
66. M. Kameyama, F. A. Siqueira, M. Garcia-Mijares, L. F. Silva, Jr., M. T. A. Silva, Molecules 2011, 16, 9421-9438
67. F. A. Siqueira, E. E. Ishikawa, A. Fogaça, A. T. Faccio, V. M. T. Carneiro, R. R. S. Soares, A. Utaka, I. R. M. Tébéka, M. Bielawski, B. Olofsson, L. F. Silva, Jr., J. Braz. Chem. Soc. 2011, 22, 1795-1807
68. A. Ahmad, L. F. Silva, Jr., Synthesis 2012, 44, 3671-3677.
69. Y. Miki, R. Fujita, K. Matsushita, J. Chem. Soc. Perkin Trans. 1998, 2533-2536.
70. H. M. C. Ferraz, A. M. Aguilar, L. F. Silva, Jr., Synthesis 2003, 1031-1034
71. L. F. Silva, Jr., E. C. Pedrozo, H. M. C. Ferraz, J. Braz. Chem. Soc. 2006, 17, 200-205.
72. F. V. Singh, J. Rehbein, T. Wirth, ChemistryOpen 2012, 1, 245-250.
73. G. A. Olah, R. D. Porter, J. Am. Chem. Soc. 1970, 92, 7627-7629
74. E. del Río, M. I. Menéndez, R. Lõpez, T. L. Sordo, J. Phys. Chem. A 2000, 104, 5568-5571.
75. R. M. Moriarty, J. S. Khosrowshahi, O. Parakash, Tetrahedron Lett. 1985, 26, 2961-2964.
76. D. J. Cram, J. Am. Chem. Soc. 1949, 71, 3863-3870
77. D. J. Cram, R. Davis, J. Am. Chem. Soc. 1949, 71, 3871-3875
78. D. J. Cram, J. Am. Chem. Soc. 1949, 71, 3875-3883
79. D. J. Cram, J. Am. Chem. Soc. 1964, 86, 3767-3772
80. H. C. Brown, K. J. Morgan, F. J. Chloupek, J. Am. Chem. Soc. 1965, 87, 2137-2153
81. P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985.
82. M. S. Yusubov, G. A. Zholobova, I. L. Filimonova, K. W. Chi, Russ. Chem. Bull. Int. Ed. 2004, 53, 1735-1742.
83. M. Fujita, M. Wakita, T. Sugimura, Chem. Commun. 2011, 47, 3983-3985.
84. T. P. Pell, S. A. Couchman, S. Ibrahim, D. J. D. Wilson, B. J. Smith, P. J. Barnard, J. L. Dutton, Inorg. Chem. 2012, 51, 13034-13040.
85. E. L. Myers, C. P. Butts, V. K. Aggarwal, Chem. Commun. 2006, 4434-4436.
86. L. P. Hammett, J. Am. Chem. Soc. 1937, 59, 96-103
87. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
88. H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876-881.
89. CCDC 929704 [(R)- 3 c ] and CCDC 929705 [(R)- 3 d ] 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.
90. Y. Nishikawa, H. Yamamoto, J. Am. Chem. Soc. 2011, 133, 8432-8435.
91. H. E. Zimmerman, A. Pushechnikov, Eur. J. Org. Chem. 2006, 3491-3497.
92. J. Richter, E. M. Landau, S. Cohen, Mol. Pharmacol. 1977, 13, 548-559
93. S. Cohen, A. Goldschmid, G. Shtacher, S. Srebrenik, S. Gitter, Mol. Pharmacol. 1975, 11, 379-385
94. N. Tomihashi, M. Yamana, T. Araki, Eur. Pat. Appl., EP0 320981A1, 1989
95. K. Wakabayashi, R. Tamai, A. Sekiya, M. Tamura, Jpn. Kokai Tokkyo Koho, JP 2001031613A, 2001.
96. J.-L. Peglion, H. Canton, K. Bervoets, V. Audinot, M. Brocco, A. Gobert, S. Le Marouille-Girardon, M. J. Millan, J. Med. Chem. 1995, 38, 4044-4055.