Organocatalytic asymmetric domino aza-michael - Mannich reaction: Synthesis of tetrahydroimidazopyrimidine derivatives

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8064-8069

  Li, Hong ^a   Zhao, Junling ^a   Zeng, Lili ^a   Hu, Wenhui ^a,b  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b State Key Laboratory of Respiratory Disease   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL CENTERS; GOOD YIELD; MANNICH REACTIONS; ORGANOCATALYTIC; UNSATURATED ALDEHYDES;

ALDEHYDES; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

ALDEHYDE; IMIDAZOLE DERIVATIVE; N ARYLIDENE 1H IMIDAZOL 2 AMINE; PYRIMIDINE DERIVATIVE; TETRAHYDROIMIDAZOPYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYSIS; CONTROLLED STUDY; DRUG ISOLATION; DRUG SELECTIVITY; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; PYRIMIDINE METABOLISM; STEREOCHEMISTRY;

AZA COMPOUNDS; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; MANNICH BASES; PROLINE; PYRIMIDINES;

EID: 80054103568     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201301p     Document Type: Article

References (49)

1. (a) Kenyon, G. L.; Rowley, G. L. J. Am. Chem. Soc. 1971, 93, 5552.
2. (b) Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Chem. Pharm. Bull. 1979, 27, 848.
3. (c) Kienzle, F.; Kaiser, A.; Chodnekar, M. S. Eur. J. Med. Chem. Chim. Ther. 1982, 17, 547.
4. (d) Roth, H. J.; Kleemann, A. In Pharmaceutical Chemistry. Vol. 1: Drug Synthesis; John Wiley & Sons: New York, 1988.
5. (a) Van Gelder, J.; Raeymaekers, A. H.; Roevens, L.; Van Laerhoven, W. U.S. Patent 3923808, 1975.
6. (b) Vrudhula, V. M.; Dasgupta, B.; Pin, S. S.; Burris, K. D.; Balanda, L. A.; Fung, L. K.; Fiedler, T.; Browman, K. E.; Taber, M. T.; Zhang, J.; Macor, J. E.; Dubowchik, G. M. Bioorg. Med. Chem. Lett. 2010, 20, 1905.
7. (c) Stahle, H.; Koppe, W. K.; Stockhaus, K.; Gaida, W.; Hoefke, W. U.S. Patent 4438118, 1984.
8. (d) Cordi, A. A.; France, S. C.; Sun, E. T.; Grove, B. U.S. Patent 5252563, 1993.
9. Pashak, R.; Batra, S. Tetrahedron 2007, 63, 9448.
10. (a) Lelais, G.; MacMillan, D.W. C. Aldrichimica Acta 2006, 39, 79.
11. (b) Special issue on organocatalysis: Chem. Rev. 2007, 107, issue 12.
12. (c) Dalko, P. I. Enantioselective Organocatalysis; Wiley-VCH: Weinheim, Germany, 2007.
13. (d) Pellisier, H. Tetrahedron 2007, 63, 9267.
14. (e) De Figueiredo, R. M.; Christmann, M. Eur. J. Org. Chem. 2007, 2575.
15. (f) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638.
16. (g) Kotsuki, H.; Ikishima, H.; Okuyama, A. Heterocycles 2008, 75, 757.
17. (h) Enders, D.; Narine, A. A. J. Org. Chem. 2008, 73, 7857.
18. (i) Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138.
19. (j) Bella, M.; Gasperi, T. Synthesis 2009, 1583.
20. (k) Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178.
21. (a) Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
22. (b) Yu, X.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037.
23. (a) Marigo, M.; Franzen, J.; Poulsen, T. B.; Zhuang, W.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964.
24. (b) Marigo, M.; Schulte, T.; Franzen, J.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
25. (c) Rueping, M.; Sugiono, E.; Merino, E. Angew. Chem., Int. Ed. 2008, 47, 3046.
26. (d) Enders, D.; Wang, C.; Bats, J. W. Angew. Chem., Int. Ed. 2008, 47, 7539.
27. (e) Zhao, G. L.; Rios, R.; Vesley, J.; Eriksson, L.; Córdova, A. Angew. Chem., Int. Ed. 2008, 47, 8468.
28. (f) Reyes, E.; Talavera, G.; Vicario, J. L.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2009, 48, 5701.
29. (g) Bencivenni, G.; Wu, L. Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M. P.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7200.
30. Grandol, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167.
31. Enders, D.; Wang, C.; Liebich, J. X. Chem.-Eur. J. 2009, 15, 11058.
32. (a) Li, H.; Wang, J.; Xie, H. X.; Zu, L. S.; Jiang, W.; Duesler, E. N.; Wang, W. Org. Lett. 2007, 9, 965.
33. (b) Sunden, H.; Rios, R.; Ibrahem, I.; Zhao, G. L.; Eriksson, L.; Cordova, A. Adv. Synth. Catal. 2007, 349, 827.
34. (c) Yoshitomi, Y.; Arai, H.; Makino, K.; Hamada, Y. Tetrahedron 2008, 64, 11568.
35. Li, H.; Zu, L. S.; Xie, H. X.; Wang, J.; Wang, W. Chem. Commun. 2008, 5636.
36. (a) Lu, M.; Zhu, D.; Lu, Y.; Hou, Y.; Tan, B.; Zhong, G. Angew. Chem., Int. Ed. 2008, 47, 10187.
37. (b) Zhu, D.; Lu, M.; Chua, J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G. Org. Lett. 2008, 10, 4585.
38. Enders, D.; Narine, A.; Toulgoat, F.; Bisschops, T. Angew. Chem., Int. Ed. 2008, 47, 5661.
39. (a) Enders, D.; Wang, C.; Raabe, G. Sythesis 2009, 4119.
40. (b) Hong, L.; Sun, W. S.; Liu, C. X.; Wang, L.; Wang, R. Chem.-Eur. J. 2010, 16, 440.
41. Bea, J.; Lee, H.; Youn, S.; Kwon, S.; Cho, C. Org. Lett. 2010, 12, 4352.
42. (a) Diner, P.; Nielsen, M.; Marigo, M.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983.
43. (b) Uria, U.; Vicario, J. L.; Badia, D.; Carrillo, L. Chem. Commun. 2007, 2509.
44. (a) Ahrendt, K. A.; Borth, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
45. (b) Northrup, A. B.; MacMillan, D.W. C. J. Am. Chem. Soc. 2002, 124, 2458.
46. List, B. Chem. Commun. 2006, 819 and references therein.
47. (a) Yoshida, M.; Mori, A.; Inaba, A.; Oka, M.; Makino, H.; Yamaguchi, M.; Fujita, H; Kawamoto, T.; Goto, M.; Kimura, H.; Baba, A.; Yasuma, T. Bioorg. Med. Chem. 2010, 18, 8501.
48. (b) Yoshida, M.; Mori, A.; Kotani, E.; Oka, M.; Makino, H.; Fujita, H; Ban, J.; Iketa, Y.; Kawamoto, T.; Goto, M.; Kimura, H.; Baba, A.; Yasuma, T. J. Med. Chem. 2011, 54, 1430.
49. Galley, G.; Groebke, Z. K.; Norcross, R.; Stalder, H. International PCT Patent Application PCT/EP2007/063153, 2008