Highly diastereo- and enantioselective Mannich reactions of synthetically flexible ketimines with secondary amine organocatalysts

Angewandte Chemie - International Edition

Volumn 51, Issue 5, 2012, Pages 1191-1194

  Kano, Taichi ^a   Song, Sunhwa ^a   Kubota, Yasushi ^b   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NIPPON SODA CO LTD   (Japan)

Author keywords

aldehydes; asymmetric catalysis; ketimines; Mannich reaction; organocatalysis

Indexed keywords

ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE; HIGH SELECTIVITY; KETIMINES; L-PROLINE; MANNICH REACTIONS; ORGANOCATALYSIS; ORGANOCATALYSTS; SECONDARY AMINES;

ALDEHYDES; AMINO ACIDS; CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS;

ORGANIC COMPOUNDS;

AMINE; IMINE; KETIMINE; MANNICH BASE; NITRILE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

AMINES; CATALYSIS; IMINES; MANNICH BASES; NITRILES; STEREOISOMERISM;

EID: 84856155924     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107375     Document Type: Article

References (63)

1. S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069
2. M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991
3. S. Kobayashi, M. Ueno, in Comprehensive Asymmetric Catalysis Supplement I (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 2003, pp. 143
4. A. E. Taggi, A. M. Hafez, T. Lectka, Acc. Chem. Res. 2003, 36, 10
5. A. Cõrdova, Acc. Chem. Res. 2004, 37, 102
6. M. M. B. Marques, Angew. Chem. 2006, 118, 356
7. Angew. Chem. Int. Ed. 2006, 45, 348
8. G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541
9. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797
10. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29
11. R. Gõmez Arrayás, J. C. Carretero, Chem. Soc. Rev. 2009, 38, 1940
12. N. Z. Burns, E. N. Jacobsen, in Science of Synthesis Stereoselective Synthesis 2 (Eds.:, J. G. De Vries, G. A. Molander, P. A. Evans,), Georg Thieme, Stuttgart, 2011, pp. 785.
13. S. Saaby, K. Nakama, M. A. Lie, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 6145
14. Y. Suto, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 500
15. R. Yazaki, T. Nitabaru, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 14477
16. Y. Du, L.-W. Xu, Y. Shimizu, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 16146
17. L. C. Wieland, E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 570
18. G. Lu, T. Yoshino, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2011, 123, 4474
19. Angew. Chem. Int. Ed. 2011, 50, 4382.
20. W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576
21. Angew. Chem. Int. Ed. 2004, 43, 4476
22. V. A. Sukach, N. M. Golovach, V. V. Pirozhenko, E. B. Rusanov, M. V. Vovk, Tetrahedron: Asymmetry 2008, 19, 761
23. B. Jiang, J. J. Dong, Y. G. Si, X. L. Zhao, Z. G. Huang, M. Xua, Adv. Synth. Catal. 2008, 350, 1360
24. C. Baudequin, A. Zamfir, S. B. Tsogoeva, Chem. Commun. 2008, 4637
25. N. Hara, R. Tamura, Y. Funahashi, S. Nakamura, Org. Lett. 2011, 13, 1662.
26. R. Bloch, Chem. Rev. 1998, 98, 1407
27. D. A. Cogan, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 268
28. O. Riant, J. Hannedouche, Org. Biomol. Chem. 2007, 5, 873
29. M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853
30. J. Clayden, M. Donnard, J. Lefranc, D. Tetlow, Chem. Commun. 2011, 47, 4624.
31. B. List, J. Am. Chem. Soc. 2000, 122, 9336
32. A. Cõrdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842
33. A. Cõrdova, S.-I. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866
34. I. Ibrahem, J. Casas, A. Cõrdova, Angew. Chem. 2004, 116, 6690
35. Angew. Chem. Int. Ed. 2004, 43, 6528
36. D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem. 2005, 117, 4147
37. Angew. Chem. Int. Ed. 2005, 44, 4079
38. J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296
39. S. Mitsumori, H. Zhang, P. H. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 1040
40. I. Ibrahem, A. Cõrdova, Chem. Commun. 2006, 1760
41. Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2006, 128, 6804
42. H. Zhang, M. Mifsud, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 9630
43. J. W. Yang, M. Stadler, B. List, Angew. Chem. 2007, 119, 615
44. Angew. Chem. Int. Ed. 2007, 46, 609
45. L. Cheng, X. Han, H. Huang, M. W. Wong, Y. Lu, Chem. Commun. 2007, 4143
46. J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List, Nature 2008, 452, 453
47. C. Gianelli, L. Sambri, A. Carlone, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8828
48. Angew. Chem. Int. Ed. 2008, 47, 8700
49. Y. Hayashi, T. Okano, T. Itoh, T. Urushima, H. Ishikawa, T. Uchimaru, Angew. Chem. 2008, 120, 9193
50. Angew. Chem. Int. Ed. 2008, 47, 9053
51. B. T. Hahn, R. Fröhlich, K. Harms, F. Glorius, Angew. Chem. 2008, 120, 10134
52. Angew. Chem. Int. Ed. 2008, 47, 9985. See also Ref. [9].
53. H. Miyabe, Y. Yamaoka, Y. Takemoto, J. Org. Chem. 2006, 71, 2099.
54. T. Kano, K. Maruoka, Chem. Commun. 2008, 5465
55. T. Kano, K. Maruoka, Bull. Chem. Soc. Jpn. 2010, 83, 1421.
56. T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408
57. T. Kano, Y. Yamaguchi, K. Maruoka, Angew. Chem. 2009, 121, 1870
58. Angew. Chem. Int. Ed. 2009, 48, 1838
59. T. Kano, Y. Yamaguchi, K. Maruoka, Chem. Eur. J. 2009, 15, 6678.
60. T. Kano, H. Sugimoto, K. Maruoka, J. Am. Chem. Soc. 2011, 133, 18130.
61. G.-N. Wang, L. Yang, L.-H. Zhang, X.-S. Ye, J. Org. Chem. 2011, 76, 2001.
62. P. Fu, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 5530
63. J. M. Janey, Y. Hsiao, J. D. Armstrong III, J. Org. Chem. 2006, 71, 390.