Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex

Journal of the American Chemical Society

Volumn 131, Issue 42, 2009, Pages 15118-15119

  Abell, Joshua P ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; ALIPHATIC ALDIMINES; ALTERNATIVE SOURCE; ALUMINUM COMPLEXES; ASYMMETRIC ADDITION; CHEMICAL EQUATIONS; CYANOFORMATE; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; KETIMINES; ORGANIC SYNTHESIS; STRECKER REACTIONS;

ALUMINA; ALUMINUM; AMINES; ENANTIOSELECTIVITY; SYNTHESIS (CHEMICAL);

CYANIDES;

ALUMINUM DERIVATIVE; CYANIDE; IMINE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; STRECKER SYNTHESIS;

CATALYSIS; CYANIDES; IMINES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 70350329294     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907268g     Document Type: Article

References (63)

1. Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
2. Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910.
3. Reviews of enantioselective Strecker reactions of imines: (a) Groger, H. Chem. Rev. 2003, 103, 2795.
4. (b) Khan, N. U. H.; Kureshy, R. I.; Abdi, S. H. R.; Agrawal, S.; Jasra, R. V. Coord. Chem. Rev. 2008, 252, 593.
5. (c) Yet, L. Angew. Chem., Int. Ed. 2001, 40, 875.
6. (d) Spino, C. Angew Chem., Int. Ed. 2004, 43, 1764.
7. (e) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
8. (f) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
9. (g) Shibasaki, M.; Kanai, M.; Mita, T. Org. React. 2008, 70, 1.
10. Recent examples of asymmetric Strecker reactions from achiral imines: (a) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
11. (b) Wen, Y.; Xiong, Y.; Chang, L.; Huang, J.; Liu, X.; Feng, X. J. Org. Chem. 2007, 72, 7715.
12. (c) Ooi, T.; Uematsu, Y.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 2548.
13. (d) Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027.
14. (e) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
15. (f) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
16. (g) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
17. (h) Wenzel, M. P.; Lalonde, M. P.; Jacobsen, E. N. Synlett 2003, 1919.
18. (i) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186.
19. (j) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
20. (k) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284.
21. (l) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 1650.
22. (m) Nakamura, S.; Sato, N.; Sugimoto, M.; Toru, T. Tetrahedron: Asymmetry 2004, 15, 1513.
23. (n) Banphavichit, V.; Mansawata, W.; Bhanthumnavin, W.; Vilaivan, T. Tetrahedron 2004, 60, 10559.
24. (o) Berkessel, A.; Mukherjee, S.; Lex, J. Synlett 2006, 41.
25. (p) Kato, N.; Mita, T.; Kanai, M.; Therrien, B.; Kawano, M.; Yamaguchi, K.; Danjo, H.; Sei, Y.; Sato, A.; Furusho, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768.
26. (q) Wung, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2007, 46, 8468.
27. (r) Byrne, J. J.; Chavarot, M.; Chavant, P.-Y.; Vallée, Y. Tetrahedron Lett. 2000, 41, 873.
28. (s) Karimi, B.; Maleki, A. Chem. Commun. 2009, 5180.
29. (t) Hatano, M.; Hattori, Y.; Furuya, Y.; Ishihara, K. Org. Lett. 2009, 11, 2321.
30. (u) Wen, Y.; Gao, B.; Fu, Y.; Dong, S.; Liu, X.; Feng, X. Chem. - Eur. J. 2008, 14, 6789.
31. (v) Shen, K.; Liu, X.; Cai, Y.; Lin, L.; Feng, X. Chem. - Eur. J. 2009, 15, 6008.
32. (w) Hou, Z.; Wang, J.; Liu, X.; Feng, X. Chem. - Eur. J. 2008, 14, 4484.
33. (x) Chen, Y.-J.; Chen, C. Tetrahedron: Asymmetry 2008, 19, 2201.
34. (y) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
35. (a) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636.
36. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021.
37. (c) Yamagiwa, N.; Tian, J.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 3413.
38. (d) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
39. (e) Casas, J.; Baeza, A.; Sansano, C.; Nájera, C.; Saá, J. M. Tetrahedron: Asymmetry 2003, 14, 197.
40. (f) Belokon, Y. N.; Blacker, A. J.; Clutterbuck, L. A.; North, M. Org. Lett. 2003, 5, 4505.
41. (g) Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C. J. Am. Chem. Soc. 2005, 127, 11592.
42. (h) Belokon, Y. N.; Ishibashi, E.; Nombra, H.; North, M. Chem. Commun. 2006, 16, 1775.
43. (a) Pan, S. C.; List, B. Org. Lett. 2007, 9, 1149.
44. (b) Pan, S. C.; Zhou, J.; List, B. Angew. Chem., Int. Ed. 2007, 46, 612.
45. Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Fini, F.; Pettersen, D.; Ricci, A. J. Org. Chem. 2006, 71, 9869.
46. (a) Takenaka, N.; Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 742.
47. (b) Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 10521.
48. Studies of the effects of protic additives in enantioselective Strecker reactions: (a) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147-3151.
49. (b) Reference 4k, l.
50. (c) Du, Y.; Xu, L.-W.; Shimizu, Y.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 16146.
51. Synthesis of TBOxH and related complexes: (a) Takenaka, N.; Xia, G. Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 13198.
52. (b) Xia, G. Y.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 2554.
53. (c) Xia, G. Y.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 496.
54. (d) Yamamoto, H.; Xia, G. Y. Chem. Lett. 2007, 36, 1082.
55. (e) Naodovic, M.; Xia, G.; Yamamoto, H. Org. Lett. 2008, 10, 4053.
56. See the Supporting Information for detailed information about the ligand, imine protecting group, and Lewis base screening.
57. North and Moberg independently reported a mechanistically related reaction with aldehydes for asymmetric cyanohydrin synthesis using a titanium SALEN dimer catalyst with alternative cyanide sources (see ref 5f, g).
58. NMR analysis of the reaction mixture (Table 1, entry 8) revealed the appearance of new ethoxy peaks [(q, 3.91) and (t, 0.97)] immediately after the addition of the catalyst to the mixture without i-PrOH. This should indicate the presence of the expected carbamate, given its mechanistic relation to ref 5f, g. Also, GC-MS analysis of the reaction mixture indicated the presence of a product with a mass corresponding to carbamate (474.8) that, after aqueous workup and column purification, was hydrolyzed to the secondary amine product in Table 1. See the Supporting Information for NMR and GC-MS charts.
59. Triethylamine provided the products in entries 13 and 14 in 56 and 68% yield, respectively.
60. Reviews of the enantioselective construction of quaternary stereocenters: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
61. (b) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
62. (c) Fuji, K. Chem. Rev. 1993, 93, 2037.
63. Connon, S. Angew. Chem., Int. Ed. 2008, 47, 1176.