Asymmetric Mannich reaction of imines derived from aliphatic and aromatic aldehydes catalyzed by diarylprolinol silyl ether

Chemistry - A European Journal

Volumn 17, Issue 30, 2011, Pages 8273-8276

  Urushima, Tatsuya ^a   Ishikawa, Hayato ^a   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

asymmetric synthesis; domino reactions; enantioselectivity; Mannich reaction; organocatalysis

Indexed keywords

AMINO ALDEHYDES; AROMATIC ALDEHYDE; ASYMMETRIC SYNTHESIS; DOMINO REACTIONS; MANNICH REACTIONS; ORGANOCATALYSIS; PRESENCE OF WATER; SILYL ETHERS;

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; ENANTIOSELECTIVITY; ETHERS; NITROGEN COMPOUNDS; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

EID: 79960298031     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101077     Document Type: Article

References (52)

1. For reviews, see S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069
2. S. E. Denmark, O. J.-C. Nicaise, in Comprehensive Asymmetric Catalysis (Ed.:, E.N. Jacobsen,), Springer, Berlin, 1999, p. 923
3. M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096
4. Angew. Chem. Int. Ed. 1998, 37, 1044
5. E. F. Kleinman, in Comprehensive Organic Synthesis, Vol.2 (Ed.:, B.M. Trost,), Pergamon Press, Oxford, 1991, Chapter 2.3, p. 893.
6. For reviews, see A. Cõrdova, Acc. Chem. Res. 2004, 37, 102
7. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580
8. M. M. B. Marques, Angew. Chem. 2006, 118, 356
9. Angew. Chem. Int. Ed. 2006, 45, 348
10. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797
11. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471.
12. B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778
13. J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048
14. J. Song, H.-W. Shih, L. Deng, Org. Lett. 2007, 9, 603
15. J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List, Nature 2008, 452, 453
16. X.-X. Yan, Q. Peng, Q. Li, K. Zhang, J. Yao, X.-L. Hou, Y.-D. Wu, J. Am. Chem. Soc. 2008, 130, 14362
17. C. Chandler, P. Galzerano, A. Michrowska, B. List, Angew. Chem. 2009, 121, 2012
18. Angew. Chem. Int. Ed. 2009, 48, 1978
19. X. Han, J. Kwiatkowski, F. Xue, K.-W. Huang, Y. Lu, Angew. Chem. 2009, 121, 7740
20. Angew. Chem. Int. Ed. 2009, 48, 7604
21. T. Kano, Y. Yamaguchi, K. Maruoka, Chem. Eur. J. 2009, 15, 6678.
22. S. Ribe, P. Wipf, Chem. Commun. 2001, 299
23. U. M. Lindström, Chem. Rev. 2002, 102, 2751
24. M. C. Pirrung, Chem. Eur. J. 2006, 12, 1312
25. Organic Reactions in Water (Ed.:, U.M. Lindstrom,), Blackwell Publishing, Oxford, 2007
26. A. Chanda, V. V. Fokin, Chem. Rev. 2009, 109, 725
27. N. Mase, C. F. Barbas III, Org. Biomol. Chem. 2010, 8, 4043.
28. Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972
29. Angew. Chem. Int. Ed. 2006, 45, 958
30. Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. 2006, 118, 5653
31. Angew. Chem. Int. Ed. 2006, 45, 5527.
32. N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734.
33. For an organocatalyst-mediated asymmetric catalytic Mannich reaction of unmodified aldehyde and N-Boc imine derived from aromatic aldehyde, see J. W. Yang, M. Stadler, B. List, Angew. Chem. 2007, 119, 615
34. Angew. Chem. Int. Ed. 2007, 46, 609
35. J. Vesely, R. Rios, I. Ibrahem, A. Cõrdova, Tetrahedron Lett. 2007, 48, 421
36. C. Gianelli, L. Sambri, A. Carlone, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8828
37. Angew. Chem. Int. Ed. 2008, 47, 8700
38. T. Kano, Y. Yamaguchi, K. Maruoka, Angew. Chem. 2009, 121, 1870
39. Angew. Chem. Int. Ed. 2009, 48, 1838
40. L. Deiana, G.-L. Zhao, P. Dziedzic, R. Rios, J. Vesely, J. Ekstrom, A. Cõrdova, Tetrahedron Lett. 2010, 51, 234
41. P. Galzerano, D. Agostino, G. Bencivenni, L. Sambri, G. Bartoli, P. Melchiorre, Chem. Eur. J. 2010, 16, 6069.
42. E. Gomez-Bengoa, M. Maestro, A. Mielgo, I. Otazo, C. Palomo, I. Velilla, Chem. Eur. J. 2010, 16, 5333.
43. F. Chemla, V. Hebbe, J.-F. Normant, Synthesis 2000, 75.
44. For the diarylprolinol silyl ether, see Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284
45. Angew. Chem. Int. Ed. 2005, 44, 4212
46. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804
47. Angew. Chem. Int. Ed. 2005, 44, 794
48. M. Marigo, D. Fielenbach, A. Braunton, A. Kjasgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769
49. Angew. Chem. Int. Ed. 2005, 44, 3703. For reviews, see A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922.
50. For reviews, see T. Kan and T. Fukuyama, J. Synth. Org. Chem. Jpn. 2001, 59, 779
51. T. Kan, T. Fukuyama, Chem. Commun. 2004, 353.
52. K. Burgess, L. T. Liu, B. Pal, J. Org. Chem. 1993, 58, 4758.