Organocatalytic direct asymmetric aldol reactions of 3-isothiocyanato oxindoles to ketones: Stereocontrolled synthesis of spirooxindoles bearing highly congested contiguous tetrasubstituted stereocenters

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2472-2475

  Chen, Wen Bing ^a,c   Wu, Zhi Jun ^b   Hu, Jing ^a   Cun, Lin Feng ^a   Zhang, Xiao Mei ^a   Yuan, Wei Cheng ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; INDOLE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; KETONE; OXINDOLE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; INDOLES; ISOTHIOCYANATES; KETONES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 79955595508     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200724q     Document Type: Article

References (62)

1. For selected reviews on aldol reactions, see: Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, p 2.
2. Carreira, E. M. In Catalytic Asymmetric Synthesis, 2 nd.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 8B2.C.
3. For selected reviews, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357
4. Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65
5. Dean, S. M.; Greenberg, W. A.; Wong, C.-H. Adv. Synth. Catal. 2007, 349, 1308
6. Mlynarski, J.; Paradowska, J. Chem. Soc. Rev. 2008, 37, 1502
7. For selected reviews on enantioselective addition to ketones, see: Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873
8. Hatano, M.; Ishihara, K. Synthesis 2008, 1647
9. Shibasaki, M.; Kanai, M. Chem. Rev 2008, 108, 2853
10. Adachi, S.; Harada, T. Eur. J. Org. Chem. 2009, 3661
11. Guthrie, J. P. J. Am. Chem. Soc. 1991, 113, 7249
12. Guthrie, J. P.; Wang, X.-P. Can. J. Chem. 1992, 70, 1055
13. For selected examples, see: Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620
14. Tokuda, O.; Kano, T.; Gao, W.-G.; Ikemoto, T.; Maruoka, K. Org. Lett. 2005, 7, 5103
15. Tang, Z.; Cun, L.-F.; Cui, X.; Mi, A. Q.; Jiang, Y.-Z.; Gong, L.-Z. Org. Lett. 2006, 8, 1263
16. Liu, J.; Yang, Z.; Wang, Z.; Wang, F.; Chen, X.; Liu, X.; Feng, X.; Su, Z.; Hu, C. J. Am. Chem. Soc. 2008, 130, 5654
17. Hara, N.; Nakamura, S.; Shibata, N.; Toru, T. Chem.-Eur. J. 2009, 15, 6790
18. For a relevant review on asymmetric enamine catalysis, see: Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
19. For selected examples, see: Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233
20. Oisaki, K.; Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644
21. Denmark, S. E.; Fan, Y.; Eastgate, M. D. J. Org. Chem. 2005, 70, 5235
22. Moreau, X.; Bazan-Tejeda, B.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 7288
23. Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7164
24. For selected examples, see: Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225
25. Deschamp, J.; Chuzel, O.; Hannedouche, J.; Riant, O. Angew. Chem., Int. Ed. 2006, 45, 1292
26. Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 1403
27. Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 14440
28. Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 7439
29. Trost, B. M.; Jiang, C. Synthesis 2006, 369
30. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969
31. Yoshino, T.; Morimoto, H.; Lu, G.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 17082
32. Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127
33. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36
34. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
35. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
36. Takasugi, M.; Monde, K.; Katsui, N.; Shirata, A. Chem. Lett. 1987, 1631
37. Gross, D.; Porzel, A.; Schmidt, J. Z. Naturforsch. 1994, 49c, 281
38. Monde, K.; Takasugi, M.; Shirata, A. Phytochemistry 1995, 39, 581
39. Monde, K.; Harada, N.; Takasugi, M.; Kutschy, P.; Suchy, M.; Dzurilla, M. J. Nat. Prod. 2000, 63, 1312
40. Monde, K.; Osawa, S.; Harada, K.; Takasugi, M.; Suchý, M.; Kutschy, P.; Dzurilla, M.; Balentová, E. Chem. Lett. 2000, 886
41. Suchý, M.; Kutschy, P.; Monde, K.; Goto, H.; Harada, N.; Takasugi, M.; Dzurilla, M.; Balenová, E. J. Org. Chem. 2001, 66, 3940
42. Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328
43. Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q. Phytochemistry 2000, 53, 161
44. Gross, D. J. Plant. Dis. Prot. 1993, 100, 433
45. Liao, Y.-H.; Zhang, H.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron: Asymmetry 2009, 20, 2397
46. Liao, Y.-H.; Chen, W.-B.; Wu, Z.-J.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2010, 352, 827
47. Chen, W.-B.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2010, 66, 1441
48. Liao, Y.-H.; Liu, X.-L.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 2896
49. Chen, W.-B.; Wu, Z.-J.; Pei, Q.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 3132
50. Liu, X.-L.; Liao, Y.-H.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2010, 75, 4872
51. For the synthesis of 3-isothiocyanato oxindoles 2, see the Supporting Information.
52. For the use of α-isothiocyanato imides as nucleophiles in the reactions with aldehydes, aldimines, and α-ketoesters, see: Willis, M. C.; Cutting, G. A.; Piccio, V. J.-D.; Durbin, M. J.; John, M. P. Angew. Chem., Int. Ed. 2005, 44, 1543
53. Cutting, G. A.; Stainforth, N. E.; John, M. P.; Kociok-Köhn, G.; Willis, M. C. J. Am. Chem. Soc. 2007, 129, 10632
54. Li, L.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 12248
55. Shi, Z.; Yu, P.; Chen, P. J.; Zhong, G. Adv. Synth. Catal. 2009, 351, 2797
56. Li, L.; Ganesh, M.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 11648
57. Jiang, X.; Zhang, G.; Fu, D.; Cao, Y.; Shen, F.; Wang, R. Org. Lett. 2010, 12, 1544
58. Vecchione, M. K.; Li, L.; Seidel, D. Chem. Commun. 2010, 46, 4604
59. Chen, X.; Zhu, Y.; Qiao, Z.; Xie, M.; Lin, L.; Liu, X.; Feng, X. Chem.-Eur. J. 2010, 16, 10124
60. CCDC 810232 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.
61. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151
62. Gueyrard, D.; Leoni, O.; Palmieri, S.; Rollin, P. Tetrahedron: Asymmetry 2001, 12, 337