Catalytic enantioselective electrophilic aminations of acyclic α-alkyl β-carbonyl nucleophiles

Synlett

Volumn , Issue 10, 2009, Pages 1685-1689

  Liu, Xiaofeng ^a   Sun, Bingfeng ^a   Deng, Li ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Asymmetric organocatalysis; Bifunctional catalysis; Chiral amines; Cinchona alkaloids; Quaternary stereocenters

Indexed keywords

ACETIC ACID DERIVATIVE; ALPHA METHYLSERINE; BETA CARBONYL DERIVATIVE; BETA KETO THIOESTER DERIVATIVE; BETA OXOCARBOXYLIC ACID ESTER; CARBONYL DERIVATIVE; CINCHONA ALKALOID; ELECTROPHILE; ESTER DERIVATIVE; NUCLEOPHILE; SERINE DERIVATIVE; THIOESTER; TRIFLUOROETHYL ALPHA METHYL ALPHA CYANOACETATE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; SUBSTITUTION REACTION;

EID: 67649380750     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217334     Document Type: Article

References (36)

1. For reviews, see: (a) Gröger, H. Chem. Rev. 2003, 103, 2795.
2. (b) Spino, C. Angew. Chem. Int. Ed. 2004, 43, 1764.
3. (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
4. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
5. (c) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
6. (d) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147.
7. (e) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153.
8. (f) Kato, N.; Tomita, D.; Maki, K.; Kanai, M.; Shibasaki, M. J. Org. Chem. 2004, 69, 6128.
9. (g) 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.
10. (h) Wang, J.; Hu, X. L.; Jiang, J.; Gou, S. H.; Huang, X.; Liu, X. H.; Feng, X. M. Angew. Chem. Int. Ed. 2007, 46, 8468.
11. (i) Hou, Z.; Wang, J.; Liu, X.; Feng, X. Chem. Eur. J. 2008, 14, 4484.
12. For reviews, see: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
13. (b) O'Donell, M. J. Acc. Chem. Res. 2004, 37, 506.
14. (c) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.
15. (a) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228.
16. (b) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716.
17. (c) Ooi, T.; Takeuchi, M.; Ohara, D.; Maruoka, K. Synlett 2001, 1185.
18. (d) Jew, S.-s.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Lee, Y.-J.; Park, B.-s.; Kim, M. G.; Park, H.-g. J. Org. Chem. 2003, 68, 4514.
19. (a) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 1367.
20. (b) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342.
21. (c) Mashiko, T.; Kumagai, N.; Shibasaki, M. Org. Lett. 2008, 10, 2725.
22. (a) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
23. (b) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
24. (c) Xu, X.; Yabuta, T.; Yuan, P.; Takemoto, Y. Synlett 2006, 137.
25. (d) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044.
26. (e) Pihko, P.; Pohjakallio, A. Synlett 2004, 2115.
27. Brandes, S.; Belle, M.; Kjærsgaard, A.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2006, 45, 1147.
28. (a) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
29. (b) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem. Int. Ed. 2004, 44, 105.
30. The β-ketothioester is more acidic than the corresponding β-ketoester, see: (a) Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218.
31. (b) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
32. (c) Bell, R. P. The Proton in Chemistry; Cornell University Press: Ithica / NY, 1959.
33. (a) Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T.; Iitaka, Y. J. Antibiot. 1991, 44, 557.
34. (b) Sano, S.; Miwa, T.; Hayashi, K.; Nozaki, K.; Ozaki, Y.; Nagao, Y. Tetrahedron Lett. 2001, 42, 4029.
35. Experimental procedure for the asymmetric amination of 3 (or 10) with 4a catalyzed by QD-1: To a solution of 3 or 10 (0.22 mmol, 1.1 equiv) and QD-1 in toluene (2.0 mL) at the indicated temperature under stirring, a solution of 4a in toluene (0.50 M, 0.40 mL, 0.20 mmol) was added dropwise in 5-10 min. The resulting reaction mixture was stirred until the color of the solution turned from yellow to colorless (or at the indicated time), and the amination product was isolated by flash chromatography.
36. Experimental procedure for the asymmetric amination of 3 (or 10) with 4a catalyzed by Q-1: A suspension of Q-1 in toluene (2.0 mL) was subjected to ultrasound until no chunky solid was visible (∼15 min). The resulting mixture was heated at 110°C until a clear solution was formed (10-15 min). While it was still hot, the solution was allowed to pass a cotton plug to remove any trace amount of insoluble residue and then cooled to room temperature. Then 3 (or 10) (0.22 mmol, 1.1 equiv) was added. This mixture was stirred at the indicated temperature and a solution of 4a (0.50 M, 0.40 mL, 0.20 mmol) in toluene was added dropwise in 5-10 min. The stirring was continued until the color of the solution turned from yellow to colorless (or at the indicated time) and the amination product was isolated by flash chromatography separation.