Silver(I)-catalyzed tandem reactions of N-activated aziridine-propargylic esters to pyrrolidin-3-one derivatives

Tetrahedron Letters

Volumn 53, Issue 46, 2012, Pages 6173-6176

  Yang, Jin Ming ^a   Zhang, Zhen ^a   Wei, Yin ^b   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,3 Acyloxy migration; 5 Exo tet cyclization; Propargylic ester; Silver catalysis; Tandem reaction

Indexed keywords

ALKYNE DERIVATIVE; AZIRIDINE; PROPARGYLIC ESTER; PYRROLIDIN 3 ONE; PYRROLIDINE DERIVATIVE; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION;

EID: 84867577299     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.09.001     Document Type: Article

References (49)

1. For recent reviews, see: Bruneau, C. Angew. Chem. 2005, 117, 2380-2386;
2. Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328-2334.
3. Marco-Contelles, J.; Soriano, E. Chem. Eur. J. 2007, 13, 1350-1357.
4. Marion, N.; Nolan, S. P. Angew. Chem. 2007, 119, 2806-2809;
5. Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752.
6. For selected papers on the gold-catalyzed reactions: Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802-5803.
7. Zhang, L. M. J. Am. Chem. Soc. 2005, 127, 16804-16805.
8. Wang, S. Z.; Zhang, L. M. J. Am. Chem. Soc. 2006, 128, 8414-8415.
9. Wang, S. Z.; Zhang, L. M. J. Am. Chem. Soc. 2006, 128, 14274-14275.
10. Jimenez-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333-346.
11. Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838-5839.
12. Luo, T.; Schreiber, S. L. Angew. Chem. 2007, 119, 8398-8401;
13. Luo, T.; Schreiber, S. L. Angew. Chem., Int. Ed. 2007, 46, 8250-8253.
14. Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718-721.
15. Teng, T.-M.; Liu, R.-S. J. Am. Chem. Soc. 2010, 132, 9298-9300.
16. For selected papers on the pt-catalyzed reactions: De Brabander, J. K.; Liu, B.; Qian, M. X. Org. Lett. 2008, 10, 2533-2536.
17. Shu, X. Z.; Ji, K. G.; Zhao, S. C.; Zheng, Z. J.; Chen, J.; Lu, L.; Liu, X. Y.; Liang, Y. M. Chem. Eur. J. 2008, 14, 10556-10559.
18. Lu, L.; Liu, X. Y.; Shu, X. Z.; Yang, K.; Ji, K. G.; Liang, Y. M. J. Org. Chem. 2009, 74, 474-477.
19. Zheng, H. J.; Zheng, J. Y.; Yu, B. X.; Chen, Q.; Wang, X. L.; He, Y. P.; Yang, Z.; She, X. G. J. Am. Chem. Soc. 2010, 132, 1788-1789.
20. For selected papers on the Rh-catalyzed reactions: Shibata, Y.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2010, 132, 7896-7898.
21. Brancour, C.; Fukuyama, T.; Ohta, Y.; Ryu, I.; Dhimane, A. L.; Fensterbank, L.; Malacria, M. Chem. Commun. 2010, 46, 5470-5472.
22. Shu, D.; Li, X.; Zhang, M.; Robichaux, P. J.; Tang, W. Angew. Chem. 2011, 123, 1382-1385;
23. Shu, D.; Li, X.; Zhang, M.; Robichaux, P. J.; Tang, W. Angew. Chem., Int. Ed. 2011, 50, 1346-1349.
24. Huang, S.; Li, X.; Lin, C. L.; Guzei, I. A.; Tang, W. Chem. Commun. 2012, 2204-2206.
25. Li, X.; Huang, S.; Schienebeck, C. M.; Shu, D.; Tang, W. Org. Lett. 2012, 14, 1584-1587.
26. Zhang, Z.; Shi, M. Eur. J. Org. Chem. 2011, 2610-2614.
27. Zhang, Z.; Shi, M. Tetrahedron Lett. 2011, 52, 6541-6544.
28. Zhao, J.; Hughes, C. O.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 7436-7437.
29. Zhang, D. H.; Yao, L. F.; Wei, Y.; Shi, M. Angew. Chem. 2011, 123, 2631-2635;
30. Zhang, D. H.; Yao, L. F.; Wei, Y.; Shi, M. Angew. Chem., Int. Ed. 2011, 50, 2583-2587.
31. Leboeuf, D.; Simonneau, A.; Aubert, C.; Malacria, M.; Gandon, V.; Fensterbank, L. Angew. Chem. 2011, 123, 7000-7003;
32. Leboeuf, D.; Simonneau, A.; Aubert, C.; Malacria, M.; Gandon, V.; Fensterbank, L. Angew. Chem., Int. Ed. 2011, 50, 6868-6871.
33. Rao, W.; Susanti, D.; Chan, P. W. H. J. Am. Chem. Soc. 2011, 133, 15248-15251.
34. Zhang, Z.; Shi, M. Chem. Eur. J. 2012, 18, 3654-3658.
35. For selected 5-exo-tet cyclization modes, see: Morimoto, Y.; Nishikawa, Y.; Ueba, C.; Tanaka, T. Angew. Chem. 2006, 118, 824-826;
36. Morimoto, Y.; Nishikawa, Y.; Ueba, C.; Tanaka, T. Angew. Chem., Int. Ed. 2006, 45, 810-812.
37. Vasconcelos, R. S.; Silva, L. F., Jr; Giannis, A. J. Org. Chem. 2011, 76, 1499-1502.
38. Uenishi, J.; Fujikura, Y.; Kawai, N. Org. Lett. 2011, 13, 2350-2353.
39. The crystal data of 2a have been deposited in CCDC with number 776038. Empirical Formula: C3.11H3.78N0.22O0.67S0.22; Formula Weight: 62.08;
40. Crystal Color, Habit: colorless, prismatic; Crystal Dimensions: 0.45 -0.33 -0.26 mm; Crystal System: Monoclinic; Lattice Type: Primitive; Lattice Parameters: a = 5.2624(2) Å, alpha = 90-; b = 11.5073(5) Å, beta = 92.5620(10) deg.; c = 22.9797(9) Å, gamma = 90-; V = 1390.17(10) Å3; Space group: P2(1)/n; Z = 18; Dcalc = 1.335 g/cm3; F000 = 592; Diffractometer: Rigaku AFC7R; Residuals: R; Rw: 0.0422, 0.1240.
41. The crystal data of 3e have been deposited in CCDC with number 802906.
42. Empirical Formula: C29H28Br2N2O6S2; Formula Weight: 724.47;
43. Crystal Color, Habit: colorless; Crystal Dimensions: 0.369 -0.345 -0.311 mm; Crystal System: Monoclinic; Lattice Type: Primitive; Lattice Parameters: a = 14.6715(16) Å, alpha = 90-; b = 11.4067(13) Å, beta = 98.450(2) deg.; c = 18.823(2) Å, gamma = 90-; V = 3115.9(6) Å3; Space group: P2(1)/n; Z = 4; Dcalc = 1.544 g/cm3; F000 = 1464; Diffractometer: Rigaku AFC7R; Residuals: R; Rw: 0.0622, 0.1622.
44. See Supporting Information.
45. Fukuyama, T.; Ohta, Y.; Brancour, C.; Miyagawa, K.; Ryu, I.; Dhimane, A.; Fensterbank, L.; Malacria, M. Chem. Eur. J. 2012, 18, 7243-7247.
46. Kikuchi, S.; Sekine, K.; Ishida, T.; Yamada, T. Angew. Chem. 2012. http://dx.doi.org/10.1002/ange.201201399;
47. Kikuchi, S.; Sekine, K.; Ishida, T.; Yamada, T. Angew. Chem., Int. Ed. 2012. http://dx.doi.org/10.1002/anie.201201399.
48. Baldwin, J. E.; Kruse, L. I. J. Chem. Soc. Chem. Commun. 1977, 233-235.
49. Baldwin, J. E.; Lusch, M. J. Tetrahedron. 1982, 38, 2939-2947. and Ref. 8