Synthesis of β-amino acid derivatives via copper-catalyzed asymmetric 1,4-reduction of β-(acylamino)acrylates

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1754-1757

  Wu, Yan ^a   Qi, Shan Bin ^a   Wu, Fei Fei ^a   Zhang, Xi Chang ^a   Li, Min ^a   Wu, Jing ^a   Chan, Albert S C ^b  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMINO ACID; COPPER; LIGAND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ACRYLATES; AMINO ACIDS; CATALYSIS; COPPER; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 79953205260     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200287z     Document Type: Article

References (54)

1. von Nussbaum, F.; Spiteller, P. In Highlights in Bioorganic Chemistry: Methods and Application; Schmuck, C., Wennemers, H., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 63 - 89.
2. Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Soloshnok, V., Eds.; John Wiley & Sons Inc: Hoboken, NJ, 2005.
3. For some recent representative reviews, see: Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035
4. Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290-4299
5. Bruneau, C.; Renaud, J.-L.; Jerphagnon, T. Coord. Chem. Rev. 2008, 252, 532-544
6. Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656-1691 and references cited therein
7. Examples include the following: Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543-554
8. Wu, J.; Chen, X.; Guo, R.; Yeung, C.-H.; Chan, A. S. C. J. Org. Chem. 2003, 68, 2490-2493
9. Qiu, L.; Wu, J.; Chan, S.; Au-Yeung, T. T.-L.; Ji, J.-X.; Guo, R.; Pai, C.-C.; Zhou, Z.; Li, X.; Fan, Q.-H.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5815-5820
10. Qiu, L.; Kwong, F. Y.; Wu, J.; Lam, W. H.; Chan, S.; Yu, W.-Y.; Li, Y.-M.; Guo, R.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955-5965
11. Examples include the following: Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64, 6907-6910
12. Yasutake, M.; Gridnev, I. D.; Higashi, N.; Imamoto, T. Org. Lett. 2001, 3, 1701-1704
13. You, J.; Drexler, H.-J.; Zhang, S.; Fischer, C.; Heller, D. Angew. Chem., Int. Ed. 2003, 42, 913-916
14. Dubrovina, N. V.; Tararov, V. I.; Monsees, A.; Spannenberg, A.; Kostas, I. D.; Börner, A. Tetrahedron: Asymmetry 2005, 16, 3640-3649
15. Reetz, M. T.; Li, X. Angew. Chem., Int. Ed. 2005, 44, 2959-2962
16. Enthaler, S.; Erre, G.; Junge, K.; Schröder, K.; Addis, D.; Michalik, D.; Hapke, M.; Redkin, D.; Beller, M. Eur. J. Org. Chem. 2008, 3352-3355
17. Examples include the following: Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159-4161
18. Lee, S.-G.; Zhang, Y. J. Org. Lett. 2002, 4, 2429-2431
19. Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553
20. Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3509-3511
21. Wu, H.-P.; Hoge, G. Org. Lett. 2004, 6, 3645-3647
22. Lefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G. Org. Lett. 2004, 6, 1733-1735
23. Hu, X.-P.; Zheng, Z. Org. Lett. 2005, 7, 419-422
24. Tang, W.; Capacci, A. G.; White, A.; Ma, S.; Rodriguez, S.; Qu, B.; Savoie, J.; Patel, N. D.; Wei, X.; Haddad, N.; Grinberg, N.; Yee, N. K.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2010, 12, 1104-1107
25. Zhang, X.; Huang, K.; Hou, G.; Cao, B.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 6421-6424
26. Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953
27. For some recent reviews, see: Riant, O.; Mostefai, N.; Courmarcel, J. Synthesis 2004, 2943-2958
28. Rendler, S.; Oestreich, M. Angew. Chem., Int. Ed. 2007, 46, 498-504
29. Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev. 2008, 108, 2916-2927
30. Lipshutz, B. H. Synlett 2009, 509-524 and references cited therein
31. Examples include the following: Moritani, Y.; Apella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797-6798
32. Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 42, 4789-4792
33. Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473-9474
34. Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253-11258
35. Lipshutz, B. H.; Servesko, J. M.; Taft, B. R. J. Am. Chem. Soc. 2004, 126, 8352-8353
36. Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793-4795
37. Czekelius, C.; Carreira, E. M. Org. Lett. 2004, 6, 4575-4577
38. Lee, D.; Kim, D.; Yun, J. Angew. Chem., Int. Ed. 2006, 45, 2785-2787
39. Llamas, T.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2007, 46, 3329-3332
40. Rainka, M. P.; Aye, Y.; Buchwald, S. L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5821-5823
41. BINAP = 2,2′-bis(diphenyllphosphino)-1,1′-binaphthyl: Noyori, R.; Takaya, H. Acc.Chem. Res. 1990, 23, 345-350
42. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008-2022
43. Deng, J.; Hu, X.-P.; Huang, J.-D.; Yu, S.-B.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2008, 73, 6022-6024
44. Wu, J.; Chan, A. S. C. Acc. Chem. Res. 2006, 39, 711-720
45. Pai, C.-C.; Lin, C.-W.; Lin, C.-C.; Chen, C.-C.; Chan, A. S. C.; Wong, W. T. J. Am. Chem. Soc. 2000, 122, 11513-11514
46. Wu, J.; Ji, J.-X.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3570-3575
47. Zhang, X.-C.; Wu, Y.; Yu, F.; Wu, F.-F.; Wu, J.; Chan, A. S. C. Chem.-Eur. J. 2009, 15, 5888-5891
48. Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640-5644
49. Hays, D. S.; Fu, G. C. Tetrahedron 1999, 55, 8815-8832
50. Sirol, S.; Courmarcel, J.; Mostefai, N.; Riant, O. Org. Lett. 2001, 3, 4111-4113
51. Mostefaï, N.; Sirol, S.; Courmarcel, J.; Riant, O. Synthesis 2007, 1265-1271
52. Wu, J.; Chen, H.; Zhou, Z.-Y.; Yeung, C.-H.; Chan, A. S. C. Synlett 2001, 1050-1054
53. Wu, J.; Chen, H.; Kwok, W.-H.; Lam, K.-H.; Zhou, Z.-Y.; Yeung, C.-H.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 1539-1543
54. Wu, J.; Pai, C.-C.; Kwok, W. H..; Guo, R. W.; Au-Yeung, T. T. L.; Yeung, C.-H.; Chan, A. S. C. Tetrahedron: Asymmetry 2003, 14, 987-992