Catalytic enantioselective desymmetrization of meso-diamines: A dual small-molecule catalysis approach

Journal of the American Chemical Society

Volumn 133, Issue 37, 2011, Pages 14538-14541

  De, Chandra Kanta ^a   Seidel, Daniel ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ANHYDRIDE; COCATALYST; DESYM-METRIZATION; ENANTIOSELECTIVE; IN-SITU; SMALL MOLECULES;

AMIDES; CATALYSTS; THIOUREAS;

ENANTIOSELECTIVITY;

4 DIMETHYLAMINOPYRIDINE; ACID ANHYDRIDE; AMIDE; BENZOIC ANHYDRIDE; DIAMINE DERIVATIVE; PYRIDINE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MOLECULE;

EID: 80052804761     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2060462     Document Type: Article

References (98)

1. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580
2. Savoia, D. Top. Organomet. Chem. 2005, 15, 1
3. Kizirian, J.-C. Chem. Rev. 2008, 108, 140
4. Faugeroux, V.; Genisson, Y. Curr. Org. Chem. 2008, 12, 751
5. Cardona, F.; Goti, A. Nat. Chem. 2009, 1, 269
6. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13
7. Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580
8. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH, Weinheim, Germany, 2005.
9. Special issue on organocatalysis: List, B. Chem. Rev. 2007, 107 (12) 5413 and subsequent articles
10. MacMillan, D. W. C. Nature 2008, 455, 304
11. Palomo, C.; Oiarbide, M.; Lopez, R. Chem. Soc. Rev. 2009, 38, 632
12. Radesca, L.; Bowen, W. D.; Dipaolo, L.; Decosta, B. R. J. Med. Chem. 1991, 34, 3058
13. De Costa, B. R.; Dominguez, C.; He, X. S.; Williams, W.; Radesca, L.; Bowen, W. J. Med. Chem. 1992, 35, 4334
14. Aicher, T. D. J. Med. Chem. 2000, 43, 236
15. Lyubomir, V. T.; Vu, B. T.; Graves, B.; Carvajal, D.; Podlaski, F.; Filipovic, Z.; Kong, N.; Kammlott, U.; Lukacs, C.; Klein, C.; Fotouhi, N.; Liu, E. A. Science 2004, 303, 844
16. Govindaraju, T.; Kumar, V. A.; Ganesh, K. N. J. Am. Chem. Soc. 2005, 127, 4144
17. Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug Design 2006, 67, 101
18. Pikul, S.; Corey, E. J. Org. Synth. 1993, 71, 22
19. Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939
20. Marques-Lopez, E.; Merino, P.; Tejero, T.; Herrera, R. P. Eur. J. Org. Chem. 2009, 2401
21. Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992
22. Rueping, M.; Antonchick, A. P. Org. Lett. 2008, 10, 1731
23. Davis, A. T.; Johnston, N. J. Chem. Sci. 2011, 2, 1076
24. Mueller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
25. Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794
26. Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410
27. Mizuta, S.; Sadamori, M.; Fujimoto, T.; Yamamoto, I. Angew. Chem., Int. Ed. 2003, 42, 3383
28. Zhao, Y.; Rodrigo, J.; Hoveyda, A. H.; Snapper, M. L. Nature 2006, 443, 67
29. Al-Sehemi, A. G. M. J. King Abdulaziz Univ., Sci. 2007, 19, 11
30. Berkessel, A.; Ong, M. C.; Nachi, M.; Neudorfl, J. M. ChemCatChem 2010, 2, 1215
31. Kitagawa, O.; Yotsumoto, K.; Kohriyama, M.; Dobashi, Y.; Taguchi, T. Org. Lett. 2004, 6, 3605
32. Kitagawa, O.; Matsuo, S.; Yotsumoto, K.; Taguchi, T. J. Org. Chem. 2006, 71, 2524
33. Luna, A.; Alfonso, I.; Gotor, V. Org. Lett. 2002, 4, 3627
34. Quijada, F. J.; Gotor, V.; Rebolledo, F. Org. Lett. 2010, 12, 3602
35. Orsat, B.; Alper, P. B.; Moree, W.; Mak, C.-P.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 712
36. Busto, E.; Gotor-Fernandez, V.; Montejo-Bernardo, J.; Garcia-Granda, S.; Gotor, V. Org. Lett. 2007, 9, 4203
37. Rios-Lombardia, N.; Busto, E.; Gotor-Fernandez, V.; Gotor, V. Eur. J. Org. Chem. 2010, 484
38. Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234
39. Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536
40. Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264
41. Anstiss, M.; Nelson, A. Org. Biomol. Chem. 2006, 4, 4135
42. Arnold, K.; Davies, B.; Hérault, D.; Whiting, A. Angew. Chem., Int. Ed. 2008, 47, 2673
43. Reznichenko, A. L.; Hampel, F.; Hultzsch, K. C. Chem. Eur. J. 2009, 15, 12819
44. Fowler, B. S.; Mikochik, P. J.; Miller, S. J. J. Am. Chem. Soc. 2010, 132, 2870
45. Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613
46. Fu, G. C. Acc. Chem. Res. 2000, 33, 412
47. France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985
48. Fu, G. C. Acc. Chem. Res. 2004, 37, 542
49. Miller, S. J. Acc. Chem. Res. 2004, 37, 601
50. Spivey, A. C.; Arseniyadis, S. Angew. Chem., Int. Ed. 2004, 43, 5436
51. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974
52. Wurz, R. P. Chem. Rev. 2007, 107, 5570
53. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
54. Kelly, T. R.; Cavero, M. Org. Lett. 2002, 4, 2653
55. Zhang, Z.; Yin, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. Org. Lett. 2003, 5, 3399
56. Verma, S. K.; Acharya, B. N.; Kaushik, M. P. Org. Lett. 2010, 12, 4232
57. De, C. K.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 17060
58. Klauber, E. G.; De, C. K.; Shah, T. K.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 13624
59. Klauber, E. G.; Mittal, N.; Shah, T. K.; Seidel, D. Org. Lett. 2011, 13, 2464
60. Birrell, J. A.; Desrosiers, J.-N.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 13872
61. Kang, S. O.; Begum, R. A.; Bowman-James, K. Angew. Chem., Int. Ed. 2006, 45, 7882
62. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, U.K., 2006; p 413.
63. Caltagirone, C.; Gale, P. A. Chem. Soc. Rev. 2009, 38, 520
64. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187
65. Gale, P. A. Chem. Commun. 2011, 47, 82
66. Kotke, M.; Schreiner, P. R. Tetrahedron 2006, 62, 434
67. Kotke, M.; Schreiner, P. R. Synthesis 2007, 779
68. Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404
69. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198
70. Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2009, 11, 887
71. Zuend, S. J.; Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 15358
72. Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, 968
73. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986
74. Schreiner, P. R. Science 2010, 327, 965
75. Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030
76. Brown, A. R.; Kuo, W.-H.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286
77. Singh, R. P.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2010, 132, 9558
78. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
79. Knowles, R. R.; Jacobsen, E. N. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20678
80. Alper, H.; Hamel, N. J. Am. Chem. Soc. 1990, 112, 2803
81. Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165
82. Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373
83. Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron: Asymmetry 2003, 14, 1995
84. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193
85. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496
86. Akiyama, T. Chem. Rev. 2007, 107, 5744
87. Rueping, M.; Antonchick, A. P.; Brinkmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903
88. Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336
89. Wang, X.; List, B. Angew. Chem., Int. Ed. 2008, 47, 1119
90. Hamilton, G. L.; Kanai, T.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 14984
91. Garcia-Garcia, P.; Lay, F.; Garcia-Garcia, P.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363
92. Lacour, J.; Moraleda, D. Chem. Commun. 2009, 7073
93. Liao, S.; List, B. Angew. Chem., Int. Ed. 2010, 49, 628
94. Yazaki, R.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 10275
95. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem. Eur. J. 2010, 16, 9350
96. Bergonzini, G.; Vera, S.; Melchiorre, P. Angew. Chem., Int. Ed. 2010, 49, 9685
97. Kim, H. Y.; Oh, K. Org. Lett. 2011, 13, 1306
98. Rueping, M.; Uria, U.; Lin, M.; Atodiresei, I. J. Am. Chem. Soc. 2011, 133, 3732