Enantioselective enolate protonation in sulfamichael addition to r-substituted n-acryloyloxazolidin-2-ones with bifunctional organocatalyst

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6520-6523

  Rana, Nirmal K ^a   Singh, Vinod K ^a,b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84055178173     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202808n     Document Type: Article

References (47)

1. (a) Mohr, J. T.; Hong, A. Y.; Stoltz, B. M. Nat. Chem. 2009, 1, 359.
2. (b) Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2004, 15, 3653.
3. (a) ApSimon, J., Ed. The Total Synthesis of Natural Products; John Wiley & Sons: Ottawa, 1992; Vol. 9.
4. (b) Jamali, F.; Mehvar, R.; Russell, A. S.;Sattari, S.;Yakimets, W.W.;Koo, J. J.Pharm. Sci. 1992, 81, 221.
5. (c) Harrison, I. T.; Lewis, B.; Nelson, P.; Rooks, W.; Roszkowoski, A.; Tomolonis, A.; Fried, J. H. J. Med. Chem. 1970, 13, 203.
6. For recent examples, see: Poisson, T.; Dalla, V.; Marsais, F.; Dupas, G.; Oudeyer, S.; Levacher, V. Angew. Chem., Int. Ed. 2007, 46, 7090.
7. (b) Cheon, C. H.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 9246.
8. (c) Poisson, T.; Gembus, V.; Dalla, V.; Oudeyer, S.; Levacher, V. J. Org. Chem. 2010, 75, 7704.
9. (d) Cheon, C. H.; Imahori, T.; Yamamoto, H. Chem. Commun. 2010, 46, 6980.
10. (e) Uraguchi, D.; Kinoshita, N.; Ooi, T. J. Am. Chem. Soc. 2010, 132, 12240.
11. For selected examples, see: (a) Duhamel L. Plaquevent J.-C. J. Am. Chem. Soc. 1978 100 7415.
12. (b) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979.
13. (c) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854.
14. For selected examples, see: (a) Vedejs E. Kruger A. W. Lee N. Sakata S. T. Stec M. Suna E. J. Am. Chem. Soc. 2000 122 4602.
15. (b) Wang, W.; Xu, M.-H.; Lei, X.-S.; Lin, G.-Q. Org. Lett. 2000, 2, 3773.
16. (c) Reynolds, N. T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406.
17. (a) Wilcke, F.-W.; Hanemann, K. J. Prakt. Chem. 1977, 319, 219.
18. (b) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S.; Sacramento, J. J. Chem. Soc., Perkin Trans. 1 2001, 3167.
19. (c) Belokon, Y. N.; Harutyunyan, S.; Vorontsov, E. V.; Peregudov, A. S.; Chrustalev, V. N.; Kochetkov, K. A.; Pripadchev, D.; Sagyan, A. S.; Beck, A. K.; Seebach, D. ARKIVOC 2004, 132.
20. (d) Hamashima, Y.; Somei, H.; Shimura, Y.; Tamura, T.; Sodeoka, M. Org. Lett. 2004, 6, 1861.
21. (e) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719
22. (f) Sibi, M. P.; Tatamidani, H.; Patil, K. Org. Lett. 2005, 7, 2571.
23. (g) Frost, C. G.; Penrose, S. D.; Lambshead, K.; Raithby, P. R.; Warren, J. E.; Gleave, R. Org. Lett. 2007, 9, 2119.
24. (h) Navarre, L.; Martinez, R; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2008, 130, 6159.
25. (i) Morita, M.; Drouin, L.; Motoki, R.; Kimura, Y.; Fujimori, I.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 3858.
26. (j) Poisson, T.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 7890.
27. (k) Duan, S.-W.; An, J.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2011, 13, 2290.
28. (a) Tsai, W.-J.; Lin, Y.-T.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1195.
29. (b) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
30. (c) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440.
31. (d) Henze, R.; Duhamel, L.; Lasne, M.-C. Tetrahedron: Asymmetry 1997, 8, 3363.
32. (e) Monteil, T.; Danvy, D.; Sihel, M.; Leroux, R.; Plaquevent, J.-C. Mini-Rev. Med. Chem. 2002, 2, 209.
33. (a) Abe, K.; Inoue, H.; Ikezaki, M.; Takeo, S. Chem. Pharm. Bull. 1971, 19, 595.
34. (b) Ondetti, M. A.; Rubin, B.; Cushman, D. W. Science 1977, 196, 441.
35. Song, C. E., Ed. Cinchona Alkaloids in Synthesis and Catalysis; WILEY-VCH Verlag GmbH & Co. KGaA: Weinheim, 2009.
36. (a) Rana, N. K.; Selvakumar, S.; Singh, V. K. J. Org. Chem. 2010, 75, 2089.
37. (b) Liu, Y.; Sun, B.; Wang, B.; Wakem, M.; Deng, L. J. Am. Chem. Soc. 2009, 131, 418.
38. (c) Dai, L.; Wang, S.-X.; Chen, F.-E Adv. Synth. Catal. 2010, 352, 2137.
39. (d) Ricci, P.; Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Adv. Synth. Catal. 2008, 350, 49.
40. (e) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem., Int. Ed. 2002, 41, 338.
41. (f) Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036.
42. (a) Kumar, A.; Salunkhe, R. V.; Rane, R. A.; Dike, S. Y. J. Chem. Soc., Chem. Commun. 1991, 485.
43. (b) Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603.
44. (c) Leow, D.; Lin, S.; Chittimalla, S. K.; Fu, X.; Tan, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5641.
45. Sibi, M. P.; Coulomb, J.; Stanley, L. M. Angew. Chem., Int. Ed. 2008, 47, 9913.
46. For details, see Supporting Information.
47. A control experiment was performed according to a reviewer's comment. We thank the reviewer for his valuable suggestion.