Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base

Advanced Synthesis and Catalysis

Volumn 351, Issue 17, 2009, Pages 2817-2821

  Terada, Masahiro ^a   Tsushima, Daisuke ^a   Nakano, Megumi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Amination; Amino acids; Asymmetric catalysis; Organocatalysis; Quaternary stereocenters

Indexed keywords

EID: 72149085696     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900594     Document Type: Article

References (52)

1. For recent reviews, see: a) Y. Ohfune, T. Shinada, Eur. J. Org. Chem. 2005, 5127-5143;
2. b) C. Cativiela, M. D. Díaz-de-Villegas, Tetrahedron: Asymmetry 2007, 18, 569-623;
3. c) H. Vogt, S. Bräse, Org. Biomol. Chem. 2007, 5, 406-430.
4. For a review, see : G. Guillena, D. J. Ramón, Tetrahedron: Asymmetry 2006, 17,1465-1492.
5. a) M. Marigo, K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1405-1407;
6. Angew. Chem. Int. Ed. 2003, 42, 1367-1369;
7. b) T. Mashiko, K. Hara, D. Tanaka, Y. Fujiwara, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 11342-11343;
8. c) T. Mashiko, N. Kumagai, M. Shibasaki, Org. Lett. 2008, 10, 2725-2728;
9. d) Y. Hasegawa, M. Watanabe, I. D. Gridnev, T Ikariya, J. Am. Chem. Soc. 2008, 130, 2158-2159;
10. e) J. Comelles, À. Pericas, M. Moreno-Mañas, A. Vallribera, G. DrudisSolé, A. Lledos, T. Parella, A. Roglans, S. García- Granda, L. Roces-Fernández, J. Org. Chem. 2007, 72, 2077-2087.
11. a) S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120-8121;
12. b) P. Pihko, A. Pohjakallio, Synlett 2004, 2115-2118;
13. c) X. Liu, H. Li, L. Deng, Org. Lett. 2005, 7, 167-169;
14. d) X. Xu, T. Yabuta, P. Yuan, Y. Takemoto, Synlett 2006, 137-140;
15. e) M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044-16045;
16. f) Y. Liu, R. Melgar-Fernndez, E. Juaristi, J. Org. Chem. 2007, 72, 1522-1525;
17. g) X. Liu, B. Sun, L. Deng, Synlett 2009, 1685-1689.
18. Also see: h) H. Vogt, S. Vanderheiden, S. Bräse, Chem. Commun. 2003, 2448-2449;
19. i) N. S. Chowdari, C. F. Barbas, III, Org. Lett. 2005, 7, 867-870;
20. j) J. T. Suri, D. D. Steiner, C. F. Barbas, III, Org. Lett. 2005, 7, 3885-3888.
21. For enantioselective construction of a quaternary stereogenic center using cyanoacetates as a nucleophilic component, see: a) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204-11205;
22. b) T. B. Poulsen, C. Alemparte, S, Saaby, M. Bella, K. A. Jørgensen, Angew. Chem. 2005, 117, 2956-2959;
23. Angew. Chem. Int. Ed. 2005, 44, 2896-2899;
24. c) H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948-8949;
25. d) T.-Y. Liu, R. Liu, Q. Chai, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Chem. Eur. J. 2007, 13, 319-327;
26. e) Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928-3930;
27. f) T. B. Poulsen, L. Bernardi, M. Bell, K. A. Jørgensen, Angew. Chem. 2006, 118, 6701-6704;
28. Angew. Chem. Int. Ed. 2006, 45, 6551-6554;
29. g) B. Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768-769;
30. h) X. Wang, M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129,1038-1039.
31. [4g]
32. a) M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454-1455;
33. b) M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112-14113;
34. c) M. Terada, M. Nakano, Heterocycles 2008, 76, 1049-1055;
35. d) M. Nakano, M. Terada, Synlett 2009, 1670-1674;
36. e) H. Ube, M. Terada, Bioorg. Med. Chem. Lett. 2009, 19, 3895-3898.
37. For reviews, see: a) T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557;
38. b) T Ishikawa, T. Kumamoto, Synthesis 2006, 737-752;
39. c) D. Leow, C.-H. Tan, Chem. Asian J. 2009, 4, 488-507.
40. For some selected examples on enantioselective catalysis by chiral guanidine bases, see: a) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956-2958;
41. Angew. Chem. Int. Ed. 2002, 41, 2832-2834;
42. b) J. Shen, T.T. Nguyen, Y.-P. Goh, W. Ye, X. Fu, J. Xu, C.-H. Tan, J. Am. Chem. Soc. 2006, 128, 13692-13693;
43. c) S. Kobayashi, R. Yazaki, K. Seki, Y. Yamashita, Angew. Chem. 2008, 120, 5695-5697;
44. Angew. Chem. Int. Ed. 2008, 47, 5613-5615;
45. d) A. Ryoda, N. Yajima, T. Haga, T. Kumamoto, W. Nakanishi, M. Kawahata, K. Yamaguchi, T. Ishikawa, J. Org. Chem. 2008, 73, 133-141;
46. e) D. Leow, L. Shishi, S. K. Chittimalla, X. Fu, C.-H. Tan, Angew. Chem. 2008, 120, 5723-5727;
47. Angew. Chem. Int. Ed. 2008, 47, 5641-5645;
48. f) Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M.W. Wong, C.- H. Tan, Angew. Chem. 2009, 121, 3681-3685;
49. Angew. Chem. Int. Ed. 2009, 48, 3627-3631;
50. g) H. Liu, D. Leow, K.-W Huang, C.-H. Tan, J. Am. Chem. Soc. 2009, 131, 7212-7213.
51. The reaction of the parent cyanoacetate (2a′), oxygen analogues of 2a, provided the corresponding product (4a′) quantitatively under the optimized conditions (see Table 2, footnote) but with much lower enantioselectivity (17% ee) than that for the thioester (2a). "chemical equation presented"
52. S. Hatakeyama, H. Matsumoto, H. Fukuyama, Y. Mukugi, H. Irie, J. Org. Chem. 1997, 62, 2275-2279.