N,N'-dioxide-scandium (III)-catalyzed asymmetric Michael addition of β,γ-unsaturated butenolides to α,β-unsaturated γ-keto esters

Advanced Synthesis and Catalysis

Volumn 355, Issue 14-15, 2013, Pages 2764-2768

  Ji, Jie ^a   Lin, Lili ^a   Zhou, Lin ^a   Zhang, Yuheng ^a   Liu, Yangbin ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a  

^a Sichuan University   (China)

Author keywords

Asymmetric catalysis; G butenolides; Michael addition; NN' dioxides; Scandium

Indexed keywords

EID: 84895172220     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300586     Document Type: Article

References (40)

1. For recent reviews of natural products containing butenolides, see: a) J. D. Sellars, P. G. Steel, Eur. J. Org. Chem. 2007, 3815
2. A. Bermejo, B. Figadère, M. Zafra-Polo, I. Barrachina, E. Estornell, D. Cortes, Nat. Prod. Rep. 2005, 22, 269
3. I. Prassas, E. P. Diamandis, Nat. Rev. Drug Discovery 2008, 7, 926
4. P. A. Roethle, D. Trauner, Nat. Prod. Rep. 2008, 25, 298
5. A. D. Rodr íguez, Tetrahedron 1995, 51, 4571
6. T. Montagnon, M. Tofi, G. Vassilikogiannakis, Acc. Chem. Res. 2008, 41, 1001
7. Y. Igarashi, H. Ogura, K. Furihata, N. Oku, C. Indananda, A. Thamchaipenet, J. Nat. Prod. 2011, 74, 670.
8. For some examples on building g-substituted butenolides with 2-silyloxyfurans, see: a) D. W. Brown, M. M. Campbell, A. P. Taylor, X. Zhang, Tetrahedron Lett. 1987, 28, 985
9. H. Kitajima, K. Ito, T. Katsuki, Tetrahedron 1997, 53, 17015
10. H. Kitajima, T. Katsuki, Synlett 1997, 568
11. H. Nishikori, K. Ito, T. Katsuki, Tetrahedron: Asymmetry 1998, 9, 1165
12. G. Desimoni, G. Faita, S. Filippone, M. Mella, M. G. Zampori, M. Zema, Tetrahedron 2001, 57, 10203
13. H. Suga, T. Kitamura, A. Kakehi, T. Baba, Chem. Commun. 2004, 1414
14. H. Yang, S. Kim, Synlett 2008, 555
15. S.P. Brown, N.C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192
16. Y. Huang, A. M. Walji, C. H. Larsen, D.W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051.
17. For some examples on building g-substituted butenolides with 2(5H)-furanones, see: a) B. M. Trost, J. Hitce, J. Am. Chem. Soc. 2009, 131, 4572
18. J. F. Wang, C. Qi, Z. M. Ge, T. M. Cheng, R. T. Li, Chem. Commun. 2010, 46, 2124
19. Y. Zhang, C. Yu, Y. Ji, W. Wang, Chem. Asian J. 2010, 5, 1303
20. H. C. Huang, F. Yu, Z. C. Jin, W. J. Li, W. B. Wu, X. M. Liang, J. X. Ye, Chem. Commun. 2010, 46, 5957
21. R. P. Singh, B. M. Foxman, L. Deng, J. Am. Chem. Soc. 2010, 132, 9558
22. J. Luo, H. Wang, X. Han, L.-W. Xu, J. Kwiatkowski, K.-W. Huang, Y. Lu, Angew. Chem. 2011, 123, 1901.
23. Angew. Chem. Int. Ed. 2011, 50, 1861
24. G. Hou, J. Yu, C. Yu, G. Wu, Z. Miao, Adv. Synth. Catal. 2013, 355, 589.
25. For recent asymmetric catalytic examples with a-angelica lactones, see: a) H.-L. Cui, J.-R. Huang, J. Lei, Z.-F. Wang, S. Chen, L. Wu, Y.-C. Chen, Org. Lett. 2010, 12, 720
26. Y. Wu, R. P. Singh, L. Deng, J. Am. Chem. Soc. 2011, 133, 12458
27. A. Quintard, A. Lefranc, A. Alexakis, Org. Lett. 2011, 13, 1540
28. L. Zhou, L. L. Lin, J. Ji, M. S. Xie, X. H. Liu, X. M. Feng, Org. Lett. 2011, 13, 3056
29. X. Huang, J. Peng, L. Dong, Y.-C. Chen, Chem. Commun. 2012, 48, 2439
30. M. S. Manna, S. Mukherjee, Chem. Eur. J. 2012, 18, 15277
31. W. Zhang, D. Tan, R. Lee, G. Tong, W. Chen, B. Qi, K.-W. Huang, C.-H. Tan, Z. Jiang, Angew. Chem. 2012, 124, 10216
32. Angew. Chem. Int. Ed. 2012, 51, 10069
33. M. S. Manna, V. Kumar, S. Mukherjee, Chem. Commun. 2012, 48, 5193.
34. For meanwhile published asymmetric catalytic studies with a-angelica lactones, see: a) D. Yang, L. Wang, D. Zhao, F. Han, B. Zhang, R. Wang, Chem. Eur. J. 2013, 19, 4691
35. U. Das, Y.-R. Chen, Y.-L. Tsai, W. Lin, Chem. Eur. J. 2013, 19, 7713
36. V. Kumar, B. Ray, P. Rathi, S. Mukherjee, Synthesis 2013, 45, 1641.
37. For recent studies on N,N'-dioxide-metal complexes in asymmetric reactions, see: a) X. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2011, 44, 574
38. X. M. Feng, X. H. Liu, in: Scandium: Compounds, Productions and Applications, Chiral Scandium Complexes in Catalytic Asymmetric Reactions, (Ed.: V. A. Greene), Nova Science New York, 2011, p 1.
39. For the X-ray single crystal structure of N,N'-dioxide-Sc (III), see: c) Y. L. Liu, D. J. Shang, X. Zhou, X. H. Liu, X. M. Feng, Chem. Eur. J. 2009, 15, 2055.
40. CCDC 929398 (3r) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.