Chiral-thiourea-catalyzed direct Mannich reaction

Synthesis

Volumn , Issue 16, 2007, Pages 2571-2575

  Yamaoka, Yousuke ^a   Miyabe, Hideto ^a   Yasui, Yoshizumi ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Enantioselective; Imine; Mannich reaction; Organocatalyst; Thiourea

Indexed keywords

DIASTEREOSELECTIVITIES; IMINES; MANNICH REACTION; ORGANOCATALYSTS;

CHIRALITY; ENANTIOSELECTIVITY; REACTION KINETICS; STEREOSELECTIVITY; THIOUREAS;

CATALYSTS;

2 ACETYL 2 [1 (TERT BUTOXYCARBONYLAMINO) 1 PHENYLMETHYL]CYCLOPENTANONE; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTANONE DERIVATIVE; DIETHYL[1 (4 BROMOPHENYL) 1 (TERT BUTOXYCARBONYLAMINO)METHYL]MALONATE; DIETHYL[1 (TERT BUTOXYCARBONYLAMINO) 1 (3 PYRIDYL)METHYL]MALONATE; DIETHYL[1 (TERT BUTOXYCARBONYLAMINO) 1 (4 METHOXYPHENYL)METHYL]MALONATE; DIETHYL[1 (TERT BUTOXYCARBONYLAMINO) 1 (4 TRIFLUOROMETHYLPHENYL)METHYL]MALONATE; IMINE; METHYL 1 [1 (TERT BUTOXYCARBONYLAMINO) 1 PHENYLMETHYL] 2 OXOCYCLOHEPTANECARBOXYLATE; METHYL 1 [1 (TERT BUTOXYCARBONYLAMINO) 1 PHENYLMETHYL] 2 OXOCYCLOHEXANECARBOXYLATE; METHYL 1 [1 (TERT BUTOXYCARBONYLAMINO) 1 PHENYLMETHYL] 2 OXOCYCLOPENTANECARBOXYLATE; METHYL 2 [1 (TERT BUTOXYCARBONYLAMINO) 1 PHENYLMETHYL] 1 OXO 2 INDANCARBOXYLATE; METHYL 2 [1 (TERT BUTOXYCARBONYLAMINO) 1 PHENYLMETHYL] 1 TETRALONE 2 CARBOXYLATE; METHYLMALONIC ACID; N BUTYLOXYCARBONYLIMINE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CHROMATOGRAPHY; ENANTIOSELECTIVITY; MANNICH REACTION; STEREOCHEMISTRY;

EID: 34548324642     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983795     Document Type: Article

References (64)

1. For recent reviews on organocatalyst chemistry, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726.
2. (b) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
3. (c) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
4. (d) Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37, 487-631.
5. (e) Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem. Int. Ed. 2005, 44, 1758.
6. (f) Special Issue on Organocatalysis: Adv. Synth. Catal. 2004, 346, 1007-1249.
7. (g) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
8. (h) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
9. (i) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520.
10. The potential of ureas and thioureas to serve as organocatalysts has recently begun to be explored by several groups, see: (a) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259.
11. (b) Curran, D. P.; Kuo, L. H. Tetrahedron Lett. 1995, 36, 6647.
12. (c) Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Curran, D. P. Tetrahedron 1995, 51, 621.
13. (d) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
14. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
15. (f) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2000, 39, 1279.
16. (g) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
17. (h) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
18. (i) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
19. (j) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
20. (k) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
21. (l) Wittkopp, A.; Schreiner, P. R. Chem. Eur. J. 2003, 9, 407.
22. For examples of urea-catalyzed reactions, see: (a) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Chem. Pharm. Bull. 2004, 52, 477.
23. (b) Maher, D. J.; Connon, S. J. Tetrahedron Lett. 2004, 45, 1301.
24. (c) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2004, 45, 5589.
25. (d) Yoon, T. P.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44, 466.
26. (e) Taylor, M. S.; Tokunaga, N.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44, 6700.
27. (f) Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964.
28. (g) Raheem, I. T.; Jacobsen, E. N. Adv. Synth. Catal. 2005, 347, 1701.
29. (h) Berkessel, A.; Cleemann, F.; Mukherjee, S.; Müller, T. N. Angew. Chem. Int. Ed. 2005, 44, 807.
30. (i) Berkessel, A.; Mukherjee, S.; Cleemann, F.; Müller, T. N. Chem. Commun. 2005, 1898.
31. (j) Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603.
32. (k) Vakulya, B.; Varga, A.; Csampai, A.; Soos, T. Org. Lett. 2005, 7, 1967.
33. (l) McCooey, S. H.; Connon, S. J. Angew. Chem. Int. Ed. 2005, 44, 6367.
34. (m) Hen-era, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem. Int. Ed. 2005, 44, 6576.
35. (n) Wang, J.; Li, H.; Yu, X.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4293.
36. (o) Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4713.
37. (p) Berkessel, A.; Cleemann, F.; Mukherjee, S. Angew. Chem. Int. Ed. 2005, 44, 7466.
38. (q) Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481.
39. (r) Tsogoeva, S. B.; Yalalov, D. A.; Hateley, M. J.; Weckbecker, C.; Huthmacher, K. Eur. J. Org. Chem. 2005, 4995.
40. (s) Sohtome, Y.; Hashimoto, Y.; Nagasawa, K. Adv. Synth. Catal. 2005, 347, 1643.
41. (t) Marcelli, T.; van der Haas, R. N. S.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem. Int. Ed. 2006, 45, 929.
42. (u) Dixon, D. J.; Richardson, R. D. Synlett 2006, 81.
43. For our studies on urea-catalyzed reactions, see: (a) Okino, T.; Hoashi, Y.; Takemoto, Y. Tetrahedron Lett. 2003, 44, 2817.
44. (b) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
45. (c) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
46. (d) Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem. Int. Ed. 2005, 44, 4032.
47. (e) Hoashi, Y.; Yabuta, T.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 9185.
48. (f) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
49. (g) Hoashi, Y.; Yabuta, T.; Yuan, P.; Miyabe, H.; Takemoto, Y. Tetrahedron 2006, 62, 365.
50. (h) Xu, X.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. Eur. J. 2006, 12, 466.
51. (i) Xu, X.; Yabuta, T.; Yuan, P.; Takemoto, Y. Synlett 2006, 137.
52. (j) Inokuma, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2006, 128, 9413.
53. (k) Miyabe, H.; Tuchida, S.; Yamauchi, M.; Takemoto, Y. Synthesis 2006, 3295.
54. For a review of catalytic asymmetric direct Mannich reactions, see: Córdova, A. Acc. Chem. Res. 2004, 37, 102.
55. For some recent examples of direct asymmetric Mannich reactions, see: (a) Ting, A.; Lou, S.; Schaus, S. E. Org. Lett. 2006, 8, 2003.
56. (b) Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.
57. (c) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem. Int. Ed. 2005, 44, 1525.
58. (d) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
59. (e) Matsunaga, S.; Yoshida, T.; Morimoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8777.
60. (f) Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2004, 43, 4476.
61. (g) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558.
62. (h) Córdova, A. Chem. Eur. J. 2004, 10, 1987.
63. (a) Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
64. (b) Tillman, A. L.; Ye, J.; Dixon, D. J. Chem. Commun. 2006, 1191.