Direct remote asymmetric bisvinylogous 1,4-additions of cyclic 2,5-dienones to nitroalkenes

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2370-2373

  Zhou, Zhi ^a   Feng, Xin ^a   Yin, Xiang ^a   Chen, Ying Chun ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b THIRD MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; NITRO DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKENES; AMINES; CATALYSIS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 84899858809     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500700d     Document Type: Article

References (56)

1. Fuson, R. C. Chem. Rev. 1935, 16, 1
2. 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. Martin, S. F. Acc. Chem. Res. 2002, 35, 895
5. Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 4479
6. Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076
7. Pansare, S. V.; Paul, E. K. Chem.-Eur. J. 2011, 17, 8770
8. Poulsen, T. B.; Alemparte, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614
9. 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
10. Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572
11. Shepherd, N. E.; Tanabe, H.; Xu, Y.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 3666
12. Feng, X.; Cui, H.-L.; Xu, S.; Wu, L.; Chen, Y.-C. Chem.-Eur. J. 2010, 16, 10309
13. Ube, H.; Shimada, N.; Terada, M. Angew. Chem., Int. Ed. 2010, 49, 1858
14. Jiang, L.; Lei, Q.; Huang, X.; Cui, H.-L.; Zhou, X.; Chen, Y.-C. Chem.-Eur. J. 2011, 17, 9489
15. Zhang, W.; Tan, D.; Lee, R.; Tong, G.; Chen, W.; Qi, B.; Huang, K.-W.; Tan, C.-H.; Jiang, Z. Angew. Chem., Int. Ed. 2012, 51, 10069
16. Curti, C.; Rassu, G.; Zambrano, V.; Pinna, L.; Pelosi, G.; Sartori, A.; Battistini, L.; Zanardi, F.; Casiraghi, G. Angew. Chem., Int. Ed. 2012, 51, 6200
17. Yin, L.; Takada, H.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2013, 52, 7310
18. Zhu, B.; Zhang, W.; Lee, R.; Han, Z.; Yang, W.; Tan, D.; Huang, K.-W.; Jiang, Z. Angew. Chem., Int. Ed. 2013, 52, 6666
19. Ratjen, L.; García-García, P.; Lay, F.; Beck, M. E.; List, B. Angew. Chem., Int. Ed. 2011, 50, 754
20. Abels, F.; Lindemann, C.; Schneider, C. Chem.-Eur. J. 2014, 20, 1964
21. Ramachary, D. B.; Reddy, Y. V. Eur. J. Org. Chem. 2012, 865
22. Bencivenni, G.; Galzerano, P.; Mazzanti, A.; Bartoli, G.; Melchiorre, P. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20642
23. Bergonzini, G.; Vera, S.; Melchiorre, P. Angew. Chem., Int. Ed. 2010, 49, 9685
24. Stiller, J.; Marqués-López, E.; Herrera, R. P.; Fröhlich, R.; Strohmann, C.; Christmann, M. Org. Lett. 2011, 13, 70
25. Cassani, C.; Melchiorre, P. Org. Lett. 2012, 14, 5590
26. Bastida, D.; Liu, Y.; Tian, X.; Escudero-Adán, E.; Melchiorre, P. Org. Lett. 2013, 15, 220
27. Jia, Z.-J.; Jiang, H.; Li, J.-L.; Gschwend, B.; Li, Q.-Z.; Yin, X.; Grouleff, J.; Chen, Y.-C.; Jørgensen, K. A. J. Am. Chem. Soc. 2011, 133, 5053
28. Jensen, K. L.; Dickmeiss, G.; Jiang, H.; Albrecht, Ł.; Jørgensen, K. A. Acc. Chem. Res. 2012, 45, 248
29. Li, J.-L.; Liu, T.-Y.; Chen, Y.-C. Acc. Chem. Res. 2012, 45, 1491
30. Arceo, E.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 5290
31. Kumar, I.; Ramaraju, P.; Mir, N. A. Org. Biomol. Chem. 2013, 11, 709
32. Jiang, H.; Albrecht, Ł.; Jørgensen, K. A. Chem. Sci. 2013, 4, 2287
33. Feng, X.; Zhou, Z.; Ma, C.; Yin, X.; Li, R.; Dong, L.; Chen, Y.-C. Angew. Chem., Int. Ed. 2013, 52, 14173
34. For an example with 2,5-dienals, see: Prieto, L.; Talavera, G.; Uria, U.; Reyes, E.; Vicario, J. L.; Carrillo, L. Chem.-Eur. J. 2014, 20, 2145
35. Clayden J. Chem. Soc. Rev. 2009, 38, 817
36. Clayden J. Chem. Soc. Rev. 2009, 38, 817See ref 6f. For selected examples, see:.
37. Zhao, Y.; Rodrigo, J.; Hoveyda, A. H.; Snapper, M. L. Nature 2006, 443, 67
38. Malkov, A. V.; Liddon, A. J. P. S.; Ramírez-López, P.; Bendová, L.; Haigh, D.; Kočovský, P. Angew. Chem., Int. Ed. 2006, 45, 1432
39. Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566
40. Lewis, C. A.; Chiu, A.; Kubryk, M.; Balsells, J.; Pollard, D.; Esser, C. K.; Murry, J.; Reamer, R. A.; Hansen, K. B.; Miller, S. J. J. Am. Chem. Soc. 2006, 128, 16454
41. Lewis, C. A.; Gustafson, J. L.; Chiu, A.; Balsells, J.; Pollard, D.; Murry, J.; Reamer, R. A.; Hansen, K. B.; Miller, S. J. J. Am. Chem. Soc. 2008, 130, 16358
42. van Leeuwen, P. W. N. M.; Rivillo, D.; Raynal, M.; Freixa, Z. J. Am. Chem. Soc. 2011, 133, 18562
43. Trost, B. M.; Morris, P. J.; Sprague, S. J. J. Am. Chem. Soc. 2012, 134, 17823
44. For a comprehensive review of cinchona-based primary aminocatalysis, see: Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 9748
45. Jia, Z.-J.; Zhou, Q.; Zhou, Q.-Q.; Chen, P.-Q.; Chen, Y.-C. Angew. Chem., Int. Ed. 2011, 50, 8638
46. Xiong, X.-F.; Zhou, Q.; Gu, J.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2012, 51, 4401
47. Xiong, X.-F.; Zhou, Q.; Gu, J.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2012, 51, 4401 See ref 7b.
48. Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170
49. Burns, N. Z.; Witten, M. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 14578
50. Lalonde, M. P.; McGowan, M. A.; Rajapaksa, N. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 1891
51. Liu, K.; Cui, H.-F.; Nie, J.; Dong, K.-Y.; Li, X.-J.; Ma, J.-A. Org. Lett. 2007, 9, 923
52. Uehara, H.; Barbas, C. F., III Angew. Chem., Int. Ed. 2009, 48, 9848
53. Serdyuk, O. V.; Heckel, C. M.; Tsogoeva, S. B. Org. Biomol. Chem. 2013, 11, 7051
54. Tian, X.; Liu, Y.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 6439
55. Tian, X.; Melchiorre, P. Angew. Chem., Int. Ed. 2013, 52, 5360
56. For a recent review on catalytic synthesis of chiral spirocyclic compounds, see: Rios, R. Chem. Soc. Rev. 2012, 41, 1060