Asymmetric N-heterocyclic carbene (NHC)-catalyzed annulation of modified enals with enolizable aldehydes

Organic Letters

Volumn 15, Issue 20, 2013, Pages 5202-5205

  Yetra, Santhivardhana Reddy ^a   Kaicharla, Trinadh ^a   Kunte, Sunita S ^a   Gonnade, Rajesh G ^a   Biju, Akkattu T ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84886300271     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4026155     Document Type: Article

References (66)

1. Wöhler, F.; Liebig, J. Ann. Pharm. 1832, 3, 249
2. Lapworth, A. J. Chem. Soc. 1903, 83, 995
3. Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm Soc. Jpn. 1943, 63, 296
4. Breslow, B. J. Am. Chem. Soc. 1958, 80, 3719
5. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743
6. Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463
7. Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 3492
8. De Sarkar, S.; Biswas, A.; Samanta, R. C.; Studer, A. Chem.-Eur. J. 2013, 19, 4664
9. Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906
10. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 351
11. Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686
12. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
13. Vora, H. U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617
14. Douglas, J.; Churchill, G.; Smith, A. D. Synthesis 2012, 44, 2295
15. Knappke, C. E. I.; Imami, A.; Jacobi von Wangelin, A. ChemCatChem 2012, 4, 937
16. Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182
17. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Vellalath, S. Chem. Soc. Rev. 2011, 40, 5336
18. Chiang, P.-C.; Bode, J. W. In N-Heterocyclic Carbenes; The Royal Society of Chemistry: London, 2011; p 399.
19. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691
20. Enders, D.; Niemeier, O.; Henseler, H. Chem. Rev. 2007, 107, 5606
21. White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124
22. Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205
23. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370
24. Rose, C. A.; Gundala, S.; Fagan, C. L.; Franz, J. F.; Connon, S. J.; Zeitler, K. Chem. Sci. 2012, 3, 735
25. Rose, C. A.; Gundala, S.; Connon, S. J.; Zeitler, K. Synthesis 2011, 190
26. O'Toole, S. E.; Rose, C. A.; Gundala, S.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2011, 76, 347
27. Jin, M. Y.; Kim, S. M.; Han, H.; Ryu, D. H.; Yang, J. W. Org. Lett. 2011, 13, 880
28. Piel, I.; Pawelczyk, M. D.; Hirano, K.; Fröhlich, R.; Glorius, F. Eur. J. Org. Chem. 2011, 5475
29. Biju, A. T.; Wurz, N. E.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 5970
30. Candish, L.; Forsyth, C. M.; Lupton, D. W. Angew. Chem., Int. Ed. 2013, 52, 9149
31. Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2013, 135, 58
32. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694
33. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176
34. Lai, C.-L.; Lee, H. M.; Hu, C.-H. Tetrahedron Lett. 2005, 46, 6265
35. Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453
36. Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587
37. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583
38. For a related work on the reaction of α,β-unsaturated esters with enolizable imines leading to dihydropyridinones that appeared during the preparation of this manuscript: Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592
39. Samanta, R. C.; De Sarkar, S.; Frøhlich, R.; Grimme, S.; Studer, A. Chem. Sci. 2013, 4, 2177
40. Samanta, R. C.; Maji, B.; De Sarkar, S.; Bergander, K.; Fröhlich, R.; Mück-Lichtenfeld, C.; Mayr, H.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 5234
41. Kravina, A. G.; Mahatthananchai, J.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 9433
42. Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494
43. Lyngvi, E.; Bode, J. W.; Schoenebeck, F. Chem. Sci. 2012, 3, 2346
44. Mahatthananchai, J.; Zheng, P.; Bode, J. W. Angew. Chem., Int. Ed. 2011, 50, 1673
45. Wanner, B.; Mahatthananchai, J.; Bode, J. W. Org. Lett. 2011, 13, 5378
46. Biswas, A.; De Sarkar, S.; Fröhlich, R.; Studer, A. Org. Lett. 2011, 13, 4966
47. Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Org. Lett. 2011, 13, 4080
48. De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266
49. Zhu, Z.-Q.; Zheng, X.-L.; Jiang, N.-F.; Wan, X.; Xiao, J.-C. Chem. Commun. 2011, 47, 8670
50. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810
51. Zhu, Z.-Q.; Xiao, J.-C. Adv. Synth. Catal. 2010, 352, 2455
52. Zeitler, K. Org. Lett. 2006, 8, 637
53. Yetra, S. R.; Bhunia, A.; Patra, A.; Mane, M. V.; Vanka, K.; Biju, A. T. Adv. Synth. Catal. 2013, 355, 1089
54. Yao, C.; Jiao, W.; Xiao, Z.; Liu, R.; Li, T.; Yu, C. Tetrahedron 2013, 69, 1133
55. Wang, X.-B.; Zou, X.-L.; Du, G.-F.; Liu, Z.-Y.; Dai, B. Tetrahedron 2012, 68, 6498
56. Zhang, B.; Feng, P.; Cui, Y.; Jiao, N. Chem. Commun. 2012, 48, 7280
57. Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chem.-Eur. J. 2012, 18, 1914
58. Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134
59. Struble, J. R.; Bode, J. W. Org. Synth. 2010, 87, 362
60. Mahatthananchai, J.; Bode, J. W. Chem. Sci. 2012, 3, 192
61. Zhao, X.; Ruhl, K. E.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 12330
62. Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M. Z.; Smith, A. D. J. Am. Chem. Soc. 2011, 133, 2714
63. Nair, V.; Paul, R. R.; Lakshmi, K. C. S.; Menon, R. S.; Jose, A.; Sinu, C. R. Tetrahedron Lett. 2011, 52, 5992
64. He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088
65. Zhang, Y.-R.; Lv, H.; Zhou, D.; Ye, S. Chem.-Eur. J. 2008, 14, 8473
66. CCDC-943669 (3j) 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.