Highly efficient asymmetric three-component vinylogous mannich reaction catalyzed by a chiral Scandium(III)N,N'-dioxide complex

Advanced Synthesis and Catalysis

Volumn 352, Issue 6, 2010, Pages 976-980

  Zhang, Qi ^a   Hui, Yonghai ^a   Zhou, Xin ^a   Lin, Lili ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a  

^a China   (China)

Author keywords

Asymmetric catalysis; Multicomponent reaction; Scandium; Silyl dienolates; Vinylogous mannich reaction

Indexed keywords

EID: 77951149887     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900877     Document Type: Article

References (33)

1. For reviews on the synthetic applications of vinylogous Mannich reaction, see: a) S. K. Bur, S. F Martin, Tetrahedron 2001, 57, 3221;
2. b) S. F. Martin, Acc. Chem. Res. 2002, 35, 895.
3. For direct catalytic AVM reactions, see: a) T. Y. Liu, H. L. Cui, X Long, B. J. Li, Y. Wu, L. S. Ding, Y. C. Chen, J. Am. Chem. Soc. 2007, 729, 1878;
4. b) B. Niess, K. A. Jørgensen, Chem. Commun. 2007, 1620;
5. c) A. Yamaguchi, S. Matsunaga, M. Shibasaki, Org. Lett. 2008, 10, 2319.
6. For catalytic AVM reactions of cyclic siloxyfurans, see: a) S. F. Martin, O. D. Lopez, Tetrahedron Lett. 1999, 40, 8949;
7. b) E. L. Carswell, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2006, 775, 7388;
8. Angew. Chem. Int. Ed. 2006, 45, 7230;
9. c) L. C. Wieland, E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 570;
10. d) H. Mandai, K. Mandai, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 750, 17961;
11. e) T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2008, 350, 399;
12. f) Z. L. Yuan, J. J. Jiang, M. Shi, Tetrahedron 2009, 65, 6001;
13. g) H. P Deng, Y. Wei, M. Shi, Adv. Synth. Catal. 2009, 357, 2897;
14. h) G. Casiraghi, F Zanardi, L. Battistini, G. Rassu, Synlett 2009, 1525.
15. a) M. Sickert, C. Schneider, Angew. Chem. 2008, 120, 3687;
16. Angew. Chem. Int. Ed. 2008, 47, 3631;
17. b) D. S. Giera, M. Sickert, C. Schneider, Org. Lett. 2008, 70, 4259.
18. A. S. González, R. G. Arrayás, M. R. Rivero, J. C. Carretero, Org. Lett. 2008, 70, 4335.
19. 3 complexes, see: a) D. J. Shang, J. G. Xin, Y. L. Liu, X. Zhou, X. H. Liu, X. M. Feng, J. Org. Chem. 2008, 73, 630;
20. b) X. Li, X. H. Liu, Y. Z. Fu, L. J. Wang, L. Zhou, X. M. Feng, Chem. Eur. J. 2008, 14, 4796;
21. c) X. Zhou, D. J. Shang, Q. Zhang, L. L. Lin, X. H. Liu, X. M. Feng, Org. Lett. 2009, 77, 1401;
22. d) Y. L. Liu, D. J. Shang, X. Zhou, X. H. Liu, X. M. Feng, Chem. Eur. J. 2009, 75, 2055;
23. e) M. Kokubo, C. Ogawa, S. Kobayashi, Angew. Chem. 2008, 720, 7015;
24. Angew. Chem. Int. Ed. 2008, 47, 6909.
25. For selected examples of asymmetric reactions catalyzed by chiral scandium complexes based on other chiral ligands, see: a) S. Kobayashi, M. Araki, I. Hachiya, J. Org. Chem. 1994, 59, 3758;
26. b) S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 726, 12236;
27. c) E. Mai, C. Schneider, Chem. Eur. J. 2007, 13, 2729;
28. d) A. Nojiri, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2008, 750, 5630, and references cited therein.
29. For some selected reports in which the chiral scandium complexes chelated with bidentate substrates, see: a) D. Yang, M. Yang, N. Y. Zhu, Org. Lett. 2003, 5, 3749;
30. b) D. A. Evans, J. Wu, J. Am. Chem. Soc. 2005, 727, 8006;
31. c) D. A. Evans, Y. Aye, J. Am. Chem. Soc. 2006, 725, 11034;
32. d) D. A. Evans, K. R. Fandrick, H. J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 729, 10029, and references cited therein.
33. Aliphatic aldehydes were also investigated. The reaction of cyclohexanecarbaldehyde sluggishly proceeded to give the corresponding products with 23% ee in 25% yield. Isobutyraldehyde and pivalaldehyde only provided the racemic products in 21% and 56% yields, respectively. The distinct performance of the aromatic and aliphatic aldimines suggested that a JT-JT interaction might exist between the aromatic aldimine and the aromatic ring of the catalyst, which played a crucial role in the asymmetric inducing of the reaction. [10] A scaled-up reaction of benzaldehyde was also performed which is thirty-fold larger (3 mmol) than the model reaction (0.1 mmol) and the vinylogous Mannich product 4a was produced with 80% ee and in 96% yield.