Facile synthesis of enantioenriched Cγ-tetrasubstituted α-amino acid derivatives via an asymmetric nucleophilic addition/protonation cascade

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2290-2293

  Duan, Shu Wen ^a   An, Jing ^a   Chen, Jia Rong ^a   Xiao, Wen Jing ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBON; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CARBON; MOLECULAR STRUCTURE; PROTONS; STEREOISOMERISM;

EID: 79955632755     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200550y     Document Type: Article

References (77)

1. For selective examples, see: Crich, D.; Banerjee, A. Acc. Chem. Res. 2007, 40, 151
2. Marti, M.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 11505
3. Larsen, T. O.; Petersen, B. O.; Duus, J. A.; Sørensen, D.; Frisvad, J. C.; Hansen, M. E. J. Nat. Prod. 2005, 68, 871
4. Kuritama, T.; Kakemoto, E.; Takehashi, N.; Imamura, K.-I.; Oyama, K.; Suzuki, E.; Harimaya, K.; Yaguchi, T.; Ozoe, Y. J. Agric. Food Chem. 2004, 52, 3884
5. Hart, D. J.; Magomedov, N. A. J. Am. Chem. Soc. 2001, 123, 5892
6. Wang, H.-J.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1998, 61, 804
7. γ tetrasubstituted α-amino acid derivatives: Takiguchi, S.; Iizuka, T.; Kumakura, Y.; Murasaki, K.; Ban, N.; Higuchi, K.; Kawasaki, T. J. Org. Chem. 2010, 75, 1126
8. Trzupek, J. D.; Lee, D.; Crowley, B. M.; Marathias, V. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2010, 132, 8506
9. Movassaghi, M.; Schmidt, M. A.; Ashenhurst, J. A. Org. Lett. 2008, 10, 4009
10. Goundry, W. R. F.; Lee, V.; Baldwin, J. E. Synlett 2006, 15, 2407
11. Lam, H. W.; Murray, G. J.; Firth, J. D. Org. Lett. 2005, 7, 5743
12. For a review, see: Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584 For recent examples, see: Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338
13. Weber, M.; Jautze, S.; Frey, W.; Peters, R. J. Am. Chem. Soc. 2010, 132, 12222
14. Alba, A.-N. R.; Companyó, X.; Valero, G.; Moyano, A.; Rios, R. Chem.-Eur. J. 2010, 16, 5354
15. Yoshino, T.; Morimoto, H.; Lu, G.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 17082
16. Uraguchi, D.; Ueki, Y.; Ooi, T. J. Am. Chem. Soc. 2008, 130, 14088
17. Moriyama, K.; Sakai, H.; Kawabata, T. Org. Lett. 2008, 10, 3883
18. For recent selected examples, see: Zhang, Q.; Cheng, M.; Hu, X.-Y.; Li, B.-G.; Ji, J.-X. J. Am. Chem. Soc. 2010, 132, 7256
19. Yamazaki, S.; Takebayashi, M.; Miyazaki, K. J. Org. Chem. 2010, 75, 1188
20. Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, 968
21. Fustero, S.; Roselló, M. S.; Rodrigo, V.; Cervera, J. F. S.; Piera, J.; Fuentes, A. S.; Pozo, C. D. Chem.-Eur. J. 2008, 14, 7019
22. Pan, S. C.; Zhou, J.; List, B. Angew. Chem., Int. Ed. 2007, 46, 612
23. For pioneering studies, see: Li, X.; Luo, S.-Z.; Cheng, J.-P. Chem.-Eur. J. 2010, 16, 14290
24. Wang, B.-M.; Wu, F.-H.; Wang, Y.; Liu, X.-F.; Deng, L. J. Am. Chem. Soc. 2007, 129, 768
25. Wang, Y.; Liu, X.-F.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928
26. Repka, L. M.; Ni, J.; Reisman, S. E. J. Am. Chem. Soc. 2010, 132, 14418
27. Tietze, L. F.; Gordon, B.; Kersten, G. M., Eds. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006. For selected reviews on cascade (domino) reactions, see: Hussian, M. M.; Walsh, P. J. Acc. Chem. Res. 2008, 41, 883
28. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
29. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
30. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354
31. Pellissier, H. Tetrahedron 2006, 62, 2143
32. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
33. Wang, X.-F.; Hua, Q.-L.; Cheng, Y.; An, X.-L.; Yang, Q.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2010, 49, 8379
34. Wang, X.-F.; Chen, J.-R.; Cao, Y.-J.; Cheng, H.-G.; Xiao, W.-J. Org. Lett. 2010, 12, 1140
35. Lu, L.-Q.; Li, F.; An, J.; Zhang, J.-J.; An, X.-L.; Hua, Q.-L.; Xiao, W.-J. Angew. Chem., Int. Ed. 2009, 48, 9542
36. Lu, L.-Q.; Cao, Y.-J.; Liu, X.-P.; An, J.; Yao, C.-J.; Ming, Z.-H.; Xiao, W.-J. J. Am. Chem. Soc. 2008, 130, 6946
37. Chen, J.-R.; Li, C.-F.; An, X.-L.; Zhang, J.-J.; Zhu, X.-Y.; Xiao, W.-J. Angew. Chem., Int. Ed. 2008, 47, 2489
38. For organocatalyzed conjugate addition/asymmetric protonations, see: Leow, D.; Lin, S.; Chittimalla, S. K.; Fu, X.; Tan, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5641
39. Rueping, M.; Theissmann, T.; Raja, S.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 1001
40. Rueping, M.; Antonchick, A. P. Angew. Chem., Int. Ed. 2007, 46, 4562
41. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683
42. For metal-catalyzed conjugate addition/asymmetric protonations, see: Morita, M.; Drouin, L.; Motoki, R.; Kimura, Y.; Fujimori, I.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 3858
43. Sibi, M. P.; Coulomb, J.; Stanley, L. M. Angew. Chem., Int. Ed. 2008, 47, 9913
44. Navarre, L.; Martinez, R.; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2008, 130, 6159
45. Sibi, M. P.; Tatamidani, H.; Patil, K. Org. Lett. 2005, 7, 2571
46. Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704
47. Moss, R. J.; Wadsworth, K. J.; Chapman, C. J.; Frost, C. G. Chem. Commun. 2004, 1984
48. Hamashima, Y.; Somei, H.; Shimura, Y.; Tamura, T.; Sodeoka, M. Org. Lett. 2004, 6, 1861
49. For reviews on enantioselective protonation, see: Mohr, J. T.; Hong, A. Y.; Stoltz, B. M. Nat. Chem. 2009, 1, 359
50. Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2004, 15, 3653 For selected examples of catalytic asymmetric protonation, see: Cheon, C. H.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 9246
51. Poisson, T.; Dalla, V.; Marsais, F.; Dupas, G.; Oudeyer, S.; Levacher, V. Angew. Chem., Int. Ed. 2007, 46, 7090
52. Yanagisawa, A.; Touge, T.; Arai, T. Angew. Chem., Int. Ed. 2005, 44, 1546
53. Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. 1997, 36, 2366
54. Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem., Int. Ed. 1993, 32, 1044
55. Zhang, F.-G.; Yang, Q.-Q.; Xuan, J.; Lu, H.-H.; Duan, S.-W.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2010, 12, 5636
56. Lu, H.-H.; Zhang, F.-G.; Meng, X.-G.; Duan, S.-W.; Xiao, W.-J. Org. Lett. 2009, 11, 3946
57. For selected examples of the catalytic asymmetric reactions with 3-substituted oxindole, see: Zhou, F.; Liu, Y.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
58. Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255
59. Liao, Y.-H.; Liu, X.-L.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 2896
60. Bui, T.; Syed, S.; Barbas, C. F. J. Am. Chem. Soc. 2009, 131, 8758
61. Jiang, K.; Peng, J.; Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 3955
62. Taylor, A. M.; Altman, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 9900
63. He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 4559
64. Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819
65. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157
66. Trost, B. M.; Frederiksen, M. U. Angew. Chem., Int. Ed. 2005, 44, 308
67. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127, 10164
68. For reviews, see: Connon, S. J. Synlett 2009, 354
69. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
70. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
71. Connon, S. J. Chem.-Eur. J. 2006, 12, 5418
72. Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621 For selected examples, see: Zu, L.-S.; Wang, J.; Li, H.; Xie, H.-X.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036
73. Berkessel, A.; Cleemann, F.; Mukherjee, S.; Müller, T. N.; Lex, J. Angew. Chem., Int. Ed. 2005, 44, 807
74. McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367
75. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967
76. Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603
77. Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun 2005, 4481