Calcium-catalyzed asymmetric synthesis of 3-tetrasubstituted oxindoles: Efficient construction of adjacent quaternary and tertiary chiral centers

Organic Letters

Volumn 17, Issue 8, 2015, Pages 2006-2009

  Shimizu, Shota ^a   Tsubogo, Tetsu ^a   Xu, Pengyu ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; OXINDOLE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; SYNTHESIS;

CALCIUM; CATALYSIS; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; QUANTUM THEORY;

EID: 84928024761     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00749     Document Type: Article

References (54)

1. Yu, B.; Yu, D.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2014, 10.1016/j.ejmech.2014.06.056
2. Kumari, G.; Nutan; Modi, M.; Gupta, S. K.; Singh, R. K. Eur. J. Med. Chem. 2011, 46, 1181
3. Rottmann, M.; McNamara, C.; Yeung, B. K. S.; Lee, M. C. S.; Zhou, B.; Russell, B.; Seitz, P.; Plouffe, D. M.; Dharia, N. V.; Tan, J.; Cohen, S. B.; Spencer, K. R.; Gonzalez-Paez, G. E.; Lakshminarayana, S. B.; Goh, A.; Suwanarusk, R.; Jegla, T.; Schmitt, E. K.; Beck, H.-P.; Brun, R.; Nosten, F.; Renia, L.; Dartois, V.; Keller, T. H.; Fidock, D. A.; Winzeler, E. A.; Diagana, T. T. Science 2010, 329, 1175
4. Yeung, B. K. S.; Zou, B.; Rottmann, M.; Lakshminarayana, S. B.; Ang, S. H.; Leong, S. Y.; Tan, J.; Wong, J.; Keller-Maerki, S.; Fischli, C.; Goh, A.; Schmitt, E. K.; Krastel, P.; Francotte, E.; Kuhen, K.; Plouffe, D.; Henson, K.; Wagner, T.; Winzeler, E. A.; Petersen, F.; Brun, R.; Dartois, V.; Diagana, T. T.; Keller, T. H. J. Med. Chem. 2010, 53, 5155
5. Vintonyak, V. V.; Warburg, K.; Kruse, H.; Grimme, S.; Hubel, K.; Rauth, D.; Waldmann, H. Angew. Chem., Int. Ed. 2010, 49, 5902
6. Fensome, A.; Adams, W. R.; Adams, A. L.; Berrodin, T. J.; Cohen, J.; Huselton, C.; Illenberger, A.; Karen, J. C.; Hudak, M. A.; Marella, A. G.; Melenski, E. G.; McComas, C. C.; Mugford, C. A.; Slayeden, O. D.; Yudt, M.; Zhang, J.; Zhang, P.; Zhu, Y.; Winneker, R. C.; Wrobel, J. E. J. Med. Chem. 2008, 51, 1861
7. Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qui, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130
8. Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, S.; Shangary, S.; Gao, W.; Qin, D.; Stukey, J.; Krajewski, K.; Roller, P. P.; Wang, S. J. Med. Chem. 2006, 49, 3432
9. Macpherson, L. J.; Dubin, A. E.; Evans, M. J.; Marr, F.; Schultz, P. G.; Cravatt, B. F.; Patapoutian, A. Nature 2007, 445, 541
10. Volk, B.; Barkóczy, J.; Hegedus, E.; Udvari, S.; Gacsályi, I.; Mezei, T.; Pallagi, K.; Kompagne, H.; Lévay, G.; Egyed, A.; Hársing, L. G., Jr.; Spedding, M.; Simig, G. J. Med. Chem. 2008, 51, 2522
11. Fuji, K. Chem. Rev. 1993, 93, 2037
12. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
13. Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591
14. Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688
15. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363
16. Ramon, D. J.; Yus, M. Curr. Org. Chem. 2004, 8, 149
17. Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943
18. Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473
19. Trost, B. M.; Jiang, C. Synthesis 2006, 369
20. Bella, M.; Gasperi, T. Synthesis 2009, 1583
21. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295
22. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593
23. Vesely, J.; Ramon, R. Chem. Soc. Rev. 2014, 43, 611
24. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
25. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
26. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
27. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104
28. Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y. C. Org. Lett. 2008, 10, 3583
29. He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 4559
30. Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y. J. J. Org. Chem. 2009, 74, 4650
31. Li, J.; Zhang, D. G.; Peng, Y. Chem. Commun. 2013, 49, 1330
32. Harder, S. Chem. Rev. 2010, 110, 3852
33. Yamashita, Y.; Kobayashi, S. Acc. Chem. Res. 2011, 44, 58
34. Yamashita, Y.; Tsubogo, T.; Kobayashi, S. Chem. Sci. 2012, 3, 967
35. Tsubogo, T.; Yamashita, Y.; Kobayashi, S. Top. Organomet. Chem. 2013, 45, 243
36. Saito, S.; Tsubogo, T.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 5364
37. Tsubogo, T.; Saito, S.; Seki, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 13321
38. Kobayashi, S.; Tsubogo, T.; Saito, S.; Yamashita, Y. Org. Lett. 2008, 10, 807
39. Tsubogo, T.; Yamashita, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2009, 48, 9117
40. Tsubogo, T.; Kano, Y.; Ikemoto, K.; Yamashita, Y.; Kobayashi, S. Tetrahedron: Asymmetry 2010, 21, 1221
41. Poisson, T.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 7890
42. Poisson, T.; Tsubogo, T.; Yamashita, Y.; Kobayashi, S. J. Org. Chem. 2010, 75, 963
43. Tsubogo, T.; Yamashita, Y.; Kobayashi, S. Chem. - Eur. J. 2012, 18, 13624
44. Hutka, M.; Tsubogo, T.; Kobayashi, S. Adv. Synth. Catal. 2013, 355, 1561
45. Tsubogo, T.; Shimizu, S.; Kobayashi, S. Chem. - Asian. J. 2013, 8, 872
46. We synthesized acetal-protected oxindoles 1e-g by a modified method. See: Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127, 10164
47. The detailed procedure is shown in the Supporting Information.
48. Hong, S.; Jung, M.; Park, Y.; Ha, M. W.; Park, C.; Lee, M.; Park, H. Chem. - Eur. J. 2013, 19, 9599
49. Goff, R. L.; Lawson, A. M.; Daïch, A.; Comesse, S. Org. Biomol. Chem. 2013, 11, 1818 See also ref 3a,3b
50. Berrée, F.; Chang, K.; Cobas, A.; Rapoport, H. J. Org. Chem. 1996, 61, 715
51. Pellegrin, C.; Weber, M.; Borschberg, H. J. Helv. Chim. Acta 1996, 79, 151
52. Trost, B. M.; Brennen, M. K. Org. Lett. 2006, 8, 2027 In our case, however, the racemization was suppressed.
53. Girard, V.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922
54. Yamamura, M.; Miyake, J.; Imamura, Y.; Nabeshima, T. Chem. Commun. 2011, 47, 6801