Highly stereoselective synthesis of 1,2,3-trisubstituted indanes via oxidative N-heterocyclic carbene-catalyzed cascades

Organic Letters

Volumn 13, Issue 18, 2011, Pages 4966-4969

  Biswas, Anup ^a   Sarkar, Suman De ^a   Fröhlich, Roland ^a   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; INDAN DERIVATIVE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS; INDANS; METHANE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 80052770020     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202108a     Document Type: Article

References (47)

1. Review: Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723
2. Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973
3. Ulmschneider, S.; Müller-Vieira, U.; Klein, C. D.; Antes, I.; Lengauer, T.; Hartmann, R. W. J. Med. Chem. 2005, 48, 1563
4. Gross, M. F.; Beaudoin, S.; McNaughton-Smith, G.; Amato, G. S.; Castle, N. A.; Huang, C.; Zou, A.; Yu, W. Bioorg. Med. Chem. Lett. 2007, 17, 2849
5. Hudson, S.; Kiankarimi, M.; Eccles, W.; Mostofi, Y. S.; Genicot, M. J.; Dwight, W.; Fleck, B. A.; Gogas, K.; Wade, W. S. Bioorg. Med. Chem. Lett. 2008, 18, 4495
6. Camps, P.; Formosa, X.; Galdeano, C.; Gómez, T.; Muñoz-Torrero, D.; Scarpellini, M.; Viayna, E.; Badia, A.; Clos, M. V.; Camins, A.; Pallàs, M.; Bartolini, M.; Mancini, F.; Andrisano, V.; Estelrich, J.; Lizondo, M.; Bidon-Chanal, A.; Luque, F. J. J. Med. Chem. 2008, 51, 3588
7. Navarro, C.; Csáky, A. G. Org. Lett. 2008, 10, 217
8. Sánchez-Larios, E.; Gravel, M. J. Org. Chem. 2009, 74, 7536
9. Kirchberg, S.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 6877
10. Yang, J. W.; Fonseca, M. T. H.; List, B. J. Am. Chem. Soc. 2005, 127, 15036
11. Phillips, E. M.; Wadamoto, M.; Chan, A.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 3107
12. Li, Y.; Wang, X.-Q.; Zheng, C.; You, S.-L. Chem. Commun. 2009, 5823
13. Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M. Z.; Smith, A. D. J. Am. Chem. Soc. 2011, 133, 2714
14. Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506
15. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
16. Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988
17. Nair, V.; Vellalath, S.; Babu, B. P. Chem Soc. Rev. 2008, 37, 2691
18. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2010, 291, 77
19. Guin, J.; De Sarkar, S.; Grimme, S.; Studer, A. Angew. Chem., Int. Ed. 2008, 47, 8727
20. De Sarkar, S.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190
21. De Sarkar, S.; Studer, A. Org. Lett. 2010, 12, 1992
22. De Sarkar, S.; Biswas, A.; Song, C. H.; Studer, A. Synthesis 2011, 12, 1974
23. Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126
24. Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518
25. Sohn, S. S.; Bode, J. W. Angew. Chem., Int. Ed. 2006, 45, 6021
26. Zeitler, K. Org. Lett. 2006, 8, 637
27. Zeitler, K.; Rose, C. A. J. Org. Chem. 2009, 74, 1759
28. Yamaki, Y.; Shigenaga, A.; Li, J.; Shimohigashi, Y.; Otaka, A. J. Org. Chem. 2009, 74, 3278
29. Wang, L.; Thai, K.; Gravel, M. Org. Lett. 2009, 11, 891
30. Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. Tetrahedron 2009, 65, 3102
31. Noonan, C.; Baragwanath, L.; Connon, S. J. Tetrahedron Lett. 2008, 49, 4003
32. Rose, C. A.; Zeitler, K. Org. Lett. 2010, 12, 4552
33. De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266
34. Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Org. Lett. 2011, 13, 4080
35. Zhu, Z.-Q.; Zheng, X.-L.; Jiang, N.-F.; Wan, X.; Xiao, J.-C. Chem. Commun. 2011, 47, 8670
36. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176
37. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694
38. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810
39. Mahatthananchai, J.; Zheng, P.; Bode, J. W. Angew. Chem., Int. Ed. 2011, 50, 1673
40. Struble, J. R.; Bode, J. W. Org. Synth. 2010, 87, 362
41. Vora, H. U.; Lathrop, S. P.; Reynolds, N. T.; Kerr, M. S.; deAlaniz, J. R.; Rovis, T. Org. Synth. 2010, 87, 350
42. Sato, M.; Kano, K.; Kitazawa, N.; Hisamichi, H.; Kaneko, C. Heterocycles 1990, 31, 1229
43. Conjugate addition in NHC-catalyzed cascade reactions: Fang, X.; Jiang, K.; Xing, C.; Hao, L.; Chi, Y. R. Angew. Chem., Int. Ed. 2011, 50, 1910
44. He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088
45. He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418
46. Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 10.1021/ol201917u
47. Walsh, P. J.; Kozlowski, M. C. Fundamentals of Asymmetric Catalysis; University Science Books: Sausalito, 2009; p 563.