A Yb(OTf)3/PEG-supported quaternary ammonium salt catalyst system for a three-component Mannich-type reaction in aqueous media

Synlett

Volumn , Issue 7, 2009, Pages 1107-1110

  Hong, Deng ^a   Yang, Yun Yun ^a   Wang, Yan Guang ^a   Lin, Xu Feng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

amino carbonyl compound; Mannich type reaction; One pot reaction; Poly(ethylene glycol); Ytterbium triflate

Indexed keywords

ALDEHYDE; AMINE; BETA AMINO CARBONYL DERIVATIVE; CARBONYL DERIVATIVE; CYCLOHEXANONE; MACROGOL; QUATERNARY AMMONIUM DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; WATER; YTTERBIUM TRIFLUOROMETHANESULFONATE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; MANNICH REACTION; ONE POT SYNTHESIS; RECYCLING; ROOM TEMPERATURE;

EID: 67649429559     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088221     Document Type: Article

References (35)

1. (a) Chao, J. L. Chem. Rev. 2005, 105, 3095.
2. (b) Li, C. J.; Chang, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
3. (c) Demko, Z. P.; Sharpless, K. B. J. Org. Chem. 2001, 66, 7945.
4. (d) Pirrung, M. C.; Sarma, K. D. J. Am. Chem. Soc. 2004, 126, 444.
5. (e) Manabe, K.; Limura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971.
6. (a) Ding, R.; Katebzadeh, K.; Roman, L.; Bergquist, K.; Lindström, U. M. J. Org. Chem. 2006, 71, 352.
7. (b) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
8. (c) Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.
9. (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044.
10. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
11. (c) Mannich, C.; Krosche, W. Arch. Pharm. 1912, 250, 674.
12. (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
13. (b) Arend, M.; Westerman, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044.
14. (c) Martin, S. F. Acc. Chem. Res. 2002, 35, 895.
15. (d) Joshi, N. S.; Whitaker, L. R.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 15942.
16. (e) Davis, F. A.; Zhang, Y.; Anilkumar, G. J. Org. Chem. 2003, 68, 8061.
17. (f) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
18. (g) Ollevier, T.; Nadeau, E. J. Org. Chem. 2004, 69, 9292.
19. (a) Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1, 1965.
20. (b) Azzizi, N.; Torkian, L.; Saidi, M. R. Org. Lett. 2006, 8, 2079.
21. (c) Ollevier, T.; Nadeau, E.; Guay-Bégin, A.-A. Tetrahedron Lett. 2006, 47, 8351.
22. (d) Gu, Y.; Ogawa, C.; Kobayashi, J.; Mori, Y.; Kobayashi, S. Angew. Chem. Int. Ed. 2006, 45, 7217.
23. (a) Cui, S. L.; Lin, X. F.; Wang, Y. G. Org. Lett. 2006, 8, 4517.
24. (b) Wang, Y. G.; Cui, S. L.; Lin, X. F. Org. Lett. 2006, 8, 1241.
25. (c) Cui, S. L.; Wang, J.; Lin, X. F.; Wang, Y. G. J. Org. Chem. 2007, 72, 7779.
26. (d) Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 4509.
27. (e) Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 3127.
28. (f) Wang, J.; Xu, F.-X.; Lin, X.-F.; Wang, Y. G. Tetrahedron Lett. 2008, 49, 5208.
29. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Org. Lett. 2000, 2, 1737.
30. (a) Loh, T. P.; Liung, S. B. K. W.; Tan, K. L.; Wei, L. L. Tetrahedron 2000, 56, 3227.
31. (b) Gennari, C.; Venturini, I.; Gislon, F.; Schimperma, G. Tetrahedron Lett. 1987, 28, 227.
32. (c) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331.
33. (d) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983.
34. (e) Ollevier, T.; Nadeau, E. Org. Biomol. Chem. 2007, 5, 3126.
35. 19BrFNO: C, 60.65, H, 5.09, N, 3.72. Found: C, 60.70, H, 5.12, N, 3.70. Compound 4g: colorless solid (anti/syn = 98:2); mp 112-