Recyclable chiral diamine-polyoxometalate (POM) acids catalyzed asymmetric direct aldol reaction of aromatic aldehydes with long-chain aliphatic ketones

Tetrahedron Letters

Volumn 52, Issue 29, 2011, Pages 3779-3781

  Gao, Qiang ^a,b   Lu, Sheng Mei ^a   Liu, Yan ^a   Li, Can ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Aldol reaction; Asymmetric organocatalysis; Chiral diamine; Long chain aliphatic ketone; Polyoxometalate acid

Indexed keywords

ACID; ALDEHYDE; ALIPHATIC KETONE; CHIRAL DIAMINE POLYOXOMETALATE ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; RECYCLING;

EID: 79959284594     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.053     Document Type: Article

References (25)

1. For reviews on aldol reactions, see: (a) Mahrwald, R. Modern Aldol Reactions; Weinheim: Wiley-VCH, 2004;
2. (b) Mahrwald, R. Aldol Reactions; Heidelberg: Springer, 2009.
3. (a) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396;
4. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260-5267.
5. For reviews on organocatalysis, see: (a) Berkessel, A.; Groger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, 2005;
6. (b) Dalko, P. I. Enantioselective Organocatalysis; Wiley-VCH: Weinheim, 2007;
7. (c) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569.
8. For reviews, see: (a) List, B. Tetrahedron 2002, 58, 5573-5590;
9. (b) List, B. Synlett 2001, 1675-1686;
10. (c) Alcaide, B.; Almendros, P. Angew. Chem., Int. Ed. 2003, 42, 858-860;
11. (d) List, B. Acc. Chem. Res. 2004, 37, 548-557;
12. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III Acc. Chem. Res. 2004, 37, 580-591;
13. (f) Saito, S.; Yamamoto, H. Acc. Chem. Res. 2004, 37, 570-579;
14. (g) Palomo, C.; Oiarbide, M.; Garcsa, J. M. Chem. Soc. Rev. 2004, 33, 65-75;
15. (h) Guillena, G.; Najera, C.; Ramon, D. J. Tetrahedron: Asymmetry 2007, 18, 2249-2293.
16. (a) Zhu, M.-K.; Xu, X.-Y.; Gong, L.-Z. Adv. Synth. Catal. 2008, 350, 1390-1396;
17. (b) Zhao, J.-F.; He, L.; Jiang, J.; Tang, Z.; Cun, L.-F.; Gong, L.-Z. Tetrahedron Lett. 2008, 49, 3372-3375.
18. (a) Luo, S.; Xu, H.; Li, J.; Zhang, L.; Cheng, J.-P. J. Am. Chem. Soc. 2007, 129, 3074-3075;
19. (b) Guillena, G.; Hita, M. C.; Najera, C.; Viozquez, S. F. J. Org. Chem. 2008, 73, 5933-5943;
20. (c) Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G. Org. Lett. 2007, 9, 1247-1250;
21. Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2006, 128, 734-735.
22. (a) Luo, S.; Li, J.; Xu, H.; Zhang, L.; Cheng, J.-P. Org. Lett. 2007, 9, 3675-3678;
23. (b) Li, J.; Hu, S.; Luo, S.; Cheng, J.-P. Eur. J. Org. Chem. 2009, 132-140;
24. (c) Li, J.; Li, X.; Zhou, P.; Zhang, L.; Luo, S.; Cheng, J.-P. Eur. J. Org. Chem. 2009, 4486-4493.
25. Kurimura, M.; Liu, H.; Sulima, A.; Hashimoto, A.; Przybyl, A. K.; Ohshima, E.; Kodato, S.; Deschamps, J. R.; Dersch, C. M.; Rothman, R. B.; Lee, Y. S.; Jacobson, A. E.; Rice, K. C. J. Med. Chem. 2008, 51, 7866-7881.