Sequential asymmetric catalysis in Michael-Michael-Michael-aldol reactions: Merging organocatalysis with photoredox catalysis in a one-pot enantioselective synthesis of highly functionalized decalines bearing a quaternary carbon stereocenter

Organic Letters

Volumn 15, Issue 24, 2013, Pages 6258-6261

  Hong, Bor Cherng ^a   Lin, Cheng Wei ^a   Liao, Wei Kai ^a   Lee, Gene Hsiang ^b  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84890921607     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403113c     Document Type: Article

References (56)

1. Yoon, T. P. ACS Catal 2013, 3, 895
2. Shia, L.; Wujiong Xia, W. Chem. Soc. Rev. 2012, 41, 7687
3. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828
4. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102
5. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527
6. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
7. Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672
8. Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Rueping, M. J. Am. Chem. Soc. 2013, 135, 1823
9. Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576
10. Sulzer-Mossé, S.; Alexakis, A. Chem. Commun. 2007, 3123
11. Vicario, J. L.; Badía, D.; Carrillo, L. Synthesis 2007, 2065
12. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701
13. Almasi, D.; Alonso, D. A.; Najera, C. Tetrahedron: Asymmetry 2007, 18, 299
14. Sulzer-Mosse, S.; Alexakis, A. Chem. Commun. 2007, 3123
15. Alonso, D. A. Organocatalyzed Conjugate Additions. In Enantioselective Organocatalyzed Reactions II; Mahrwald, R., Ed.; Springer: Dordrecht, 2011; Chapter 2, pp 41-185.
16. Quintard, A.; Lefranc, A.; Alexakis, A. Org. Lett. 2011, 13, 1540
17. Ooi, T.; Doda, K.; Maruoka, K. J. Am. Soc. Chem. 2003, 125, 9022
18. Galzerano, P.; Pesciaioli, F.; Mazzanti, A.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7892
19. Fu, N.; Zhang, L.; Li, J.; Luo, S.; Cheng, J.-P. Angew. Chem., Int. Ed. 2011, 50, 11451
20. King, H. D.; Meng, Z.; Denhart, D.; Mattson, R.; Kimura, R.; Wu, D.; Gao, Q.; Macor, J. E. Org. Lett. 2005, 7, 3437
21. Guo, L.; Zhang, W.; Guzei, I. A.; Spencer, L. C.; Gellman, S. H. Org. Lett. 2012, 14, 2582
22. Malihi, F.; Clive, D. L. J.; Chang, C.-C. J. Org. Chem. 2013, 78, 996
23. Singh, A. K.; Chawla, R.; Rai, A.; Yadav, L. D. S. Chem. Commun. 2012, 48, 3766
24. Kravina, A. G.; Mahatthananchai, J.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 9433
25. Clive, D. L. J.; Liu, D. Angew. Chem., Int. Ed. 2007, 46, 3738
26. For a recent review in organocatalyzed cycloadditions, see: Hong, B.-C. Organocatalyzed Cycloadditions. In Enantioselective Organocatalyzed Reactions II; Mahrwald, R., Ed.; Springer: Dordrecht, 2011; Chapter 3, pp 187-244.
27. Dange, N. S.; Hong, B.-C.; Lee, C.-C.; Lee, G.-H. Org. Lett. 2013, 15, 3914
28. Hong, B.-C.; Liao, W.-K.; Dange, N. S.; Liao, J.-H. Org. Lett. 2013, 15, 468
29. Hong, B.-C.; Dange, N. S.; Yen, P.-J.; G.-H. Lee, G.-H.; Liao, J.-H. Org. Lett. 2012, 14, 5346
30. Hong, B.-C.; Chen, P.-Y.; Kotame, P.; Lu, P.-Y.; Lee, G.-H.; JLiao, J.-H. Chem. Commun. 2012, 48, 7790
31. Hong, B.-C.; Dange, N. S.; Ding, C.-F.; Liao, J.-H. Org. Lett. 2012, 14, 448
32. Hong, B.-C.; Hsu, C.-S.; Lee, G.-H. Chem. Commun. 2012, 48, 2385
33. Hong, B.-C.; Kotame, P.; Lee, G.-H. Org. Lett. 2011, 13, 5758
34. Hong, B.-C.; Dange, N. S.; Hsu, C.-S.; Liao, J.-H.; Lee, G.-H. Org. Lett. 2011, 13, 1338
35. Hong, B.-C.; Nimje, R. Y.; Lin, C.-W.; Liao, J.-H. Org. Lett. 2011, 13, 1278 and references cited therein
36. Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211
37. Zhou, J. Chem.-Asian J. 2010, 5, 422
38. Wende, R. C.; Schreiner, P. R. Green Chem. 2012, 14, 1821
39. Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337
40. Loh, C. C.; Enders, D. Chem.-Eur. J. 2012, 18, 10212
41. Patil, N. T. Angew. Chem., Int. Ed. 2011, 50, 1759
42. Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 16, 2999
43. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
44. Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633
45. Nicewics, D. A.; MacMillan, W. C. Science 2008, 322, 77
46. Shih, H.-W.; Wal, M. N. V.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600
47. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
48. Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951
49. Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C.; MacMillan, D. W. C. Science 2013, 339, 1593
50. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094
51. For an addition of the α-aminoalkyl radical to electron-deficient alkenes by visible-light photoredox catalysts, see: Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338
52. Hong, B.-C.; Liao, W.-K.; Dange, N. S.; Liao, J.-H. Org. Lett. 2013, 15, 468
53. Hong, B.-C.; Sadani, A. A.; Nimje, R. Y.; Dange, N. S.; Lee, G.-H. Synthesis 2011, 12, 1887
54. Cai, S.; Zhang, S.; Zhao, Y.; Wang, D. Z. Org. Lett. 2013, 15, 2660
55. Morrison, J.; Osthoff, H.; Wan, P. Photochem. Photobiol. Sci. 2002, 1, 384
56. Wu, W.; Wen, L.; Shen, L.; Liang, R.; Yuan, R.; Wu, L. Appl. Catal., B 2013, 130-131, 163