Organocatalytic direct asymmetric vinylogous Michael reaction of an α,β-unsaturated γ-butyrolactam with enones

Journal of Organic Chemistry

Volumn 76, Issue 5, 2011, Pages 1472-1474

  Zhang, Yong ^a   Shao, Yong Liang ^a   Xu, Hai Sen ^a   Wang, Wei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL; DIASTEREO- AND ENANTIOSELECTIVITY; MICHAEL ADDITIONS; MICHAEL REACTIONS; ORGANOCATALYTIC; TERTIARY AMINE;

ENANTIOSELECTIVITY; THIOUREAS; UREA;

ADDITION REACTIONS;

2 PYRROLIDINONE; TERTIARY AMINE; THIOUREA;

ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; MICHAEL ADDITION;

AMINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; KETONES; LACTAMS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; THIOUREA;

EID: 79952132240     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102223v     Document Type: Article

References (45)

1. Review: Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Synlett 2009, 1525
2. Reviews: Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929
3. Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682
4. Kalesse, M. Top. Curr. Chem. 2005, 244, 43 Selected examples: Sedelmeier, J.; Hammerer, T.; Bolm, C. Org. Lett. 2008, 10, 917
5. Zhu, N.; Ma, B.-C.; Zhang, Y.; Wang, W. Adv. Synth. Catal. 2010, 352, 1291
6. Singh, R. P.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2010, 132, 9558
7. Reviews: Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221
8. Martin, S. F. Acc. Chem. Res. 2002, 35, 895 Selected examples: Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230
9. Akiyama, T.; Honma, Y.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2008, 350, 399
10. Mandai, H.; Mandai, K.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 17961
11. Sickert, M.; Abels, F.; Lang, M.; Sieler, J.; Birkemeyer, C.; Schneider, C. Chem.-Eur. J. 2010, 16, 2806
12. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192 and references therein
13. Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2008, 10, 2319
14. Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572
15. Cui, H.-L.; Huang, J.-R.; Lei, J.; Wang, Z.-F.; Chen, S.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 720
16. Wang, J.; Qi, C.; Ge, Z.; Cheng, T.; Li, R. Chem. Commun. 2010, 46, 2124
17. Zhang, Y.; Yu, C.; Ji, Y.; Wang, W. Chem. Asian J. 2010, 5, 1303
18. Huang, H.; Yu, F.; Jin, Z.; Li, W.; Wu, W.; Liang, X.; Ye, J. Chem. Commun. 2010, 46, 5957
19. Ube, H.; Shimada, N.; Terada, M. Angew. Chem., Int. Ed. 2010, 49, 1858
20. Yang, Y.; Zheng, K; Zhao, J. N.; Shi, J.; Lin, L. L.; Liu, X. H.; Feng, X. M. J. Org. Chem. 2010, 75, 5382
21. For the reactions of α,α-dicyanoalkene, see a recent review: Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 4479 Selected examples: Xue, D.; Chen, Y.-C.; Wang, Q.-W.; Cun, L.-F.; Zhu, J.; Deng, J.-G. Org. Lett. 2005, 7, 5293
22. Poulsen, T. B.; Alemparte, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614
23. Xie, J.-W.; Yue, L.; Xue, D.; Ma, X.-L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Chem. Commun. 2006, 1563
24. Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389
25. Liu, T.-Y.; Cui, H.-L.; Long, J.; Li, B.-J.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. J. Am. Chem. Soc. 2007, 129, 1878
26. Aleman, J.; Jacobsen, C. B.; Frisch, K.; Overgaard, J.; Jørgensen, K. A. Chem. Commun. 2008, 632
27. Reviews: Michael, J. P. Nat. Prod. Rep. 2008, 25, 139
28. Pyne, S. G.; Davis, A. S.; Gates, N. J.; Hartley, J. P.; Lindsay, K. B.; Machan, T.; Tang, M. Synlett 2004, 2670
29. Cheng, Y.; Huang, Z.-T.; Wang, M. X. Curr. Org. Chem. 2004, 8, 325
30. For racemic direct-type vinylogous reactions of α,β- unsaturated γ-butyrolactam and related donors, see: Sartori, A.; Curti, C.; Battistini, L.; Burreddu, P.; Rassu, G.; Pelosi, G.; Casiraghi, G.; Zanardi, F. Tetrahedron 2008, 64, 11697
31. Curti, C.; Sartori, A.; Battistini, L.; Rassu, G.; Burreddu, P.; Zanardi, F.; Casiraghi, G. J. Org. Chem. 2008, 73, 5446
32. Shepherd, N. E.; Tanabe, H.; Xu, Y.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 3666
33. Feng, X.; Cui, H.-L.; Xu, S.; Wu, L.; Chen, Y.-C. Chem.-Eur. J. 2010, 16, 10309
34. Reviews: Tian, S.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621
35. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299
36. Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
37. Connon, S. J. Chem.-Eur. J. 2006, 12, 5418
38. Marcelli, T.; van Maarseveen, J.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 7496
39. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
40. Akiyama, T. Chem. Rev. 2007, 107, 5744
41. Connon, S. J. Chem. Commun. 2008, 2499
42. For the original report on the application of cinchona alkaloid-based thiourea catalysts for the activation of chalcones, see: Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967
43. Gheorghe, A.; Schulte, M.; Reiser, O. J. Org. Chem. 2006, 71, 2173
44. As shown in Figure 2, the ee values of isolated 3q′ (40% yield) and recovered 3q (55% yield) were both kept as 99% after epimerization, indicating that only the chiral center of C5 in 3q was epimerised in the presence of DBU. See Supporting Information for characterization details.
45. Hamza, A.; Schubert, G.; Soós, T.; Pápai, I. J. Am. Chem. Soc. 2006, 128, 13151