[3 + 2] cycloaddition on carbohydrate templates: Stereoselective synthesis of pyrrolidines

Organic Letters

Volumn 13, Issue 5, 2011, Pages 1072-1075

  Cai, Shuting ^a   Kishan Gorityala, Bala ^a   Ma, Jimei ^a   Leow, Min Li ^a   Liu, Xue Wei ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; PYRROLIDINE DERIVATIVE; SILANE DERIVATIVE;

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

CARBOHYDRATES; CATALYSIS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLIDINES; SILANES; STEREOISOMERISM;

EID: 79952158476     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103119u     Document Type: Article

References (41)

1. Cheng, Y.; Huang, Z. T.; Wang, M. X. Curr. Org. Chem. 2004, 8, 325
2. Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479
3. Bianco, A.; Maggini, M.; Scorrano, G.; Toniolo, C.; Marconi, G.; Villani, C.; Prato, M. J. Am. Chem. Soc. 1996, 118, 4072
4. Royles, B. J. L. Chem. Rev. 1995, 95, 1981
5. Moloney, M. G.; Trippier, P. C.; Yaqoob, M.; Wang, Z. Curr. Drug Discovery Technol. 2004, 1, 181
6. Domagala, J. M.; Hagen, S. E.; Joannides, T.; Kiely, J. S.; Laborde, E.; Schroeder, M. C.; Sesnie, J. A.; Shapiro, M. A.; Suto, M. J.; Vanderroest, S. J. Med. Chem. 1993, 36, 871
7. Johnston, G. A. R.; Curtis, D. R.; Davies, J.; McCulloch, R. M. Nature 1974, 248, 804
8. Hussaini, S. R.; Moloney, M. G. Org. Biomol. Chem. 2003, 1, 1838
9. Blanco, M. J.; Sardina, F. J. Tetrahedron Lett. 1994, 35, 8493
10. Cren, S.; Gurcha, S. S.; Blake, A. J.; Besra, G. S.; Thomas, N. R. Org. Biomol. Chem. 2004, 2, 2418
11. Giard, T.; Lasne, M.-C.; Plaquevent, J.-C. Tetrahedron Lett. 1999, 40, 5495
12. Ibnusaud, I.; Thomas, G. Tetrahedron Lett. 2003, 44, 1247
13. Terada, Y.; Arisawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 4063
14. Karlsson, S.; Högberg, H.-E. Tetrahedron: Asymmetry 2001, 12, 1975
15. Kumar, A.; Gupta, G.; Srivastava, S. J. Comb. Chem. 2010, 12, 458
16. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835
17. Vasella, A. Helv. Chim. Acta 1977, 60, 1273
18. Kunz, H.; Müller, B.; Schanzenbach, D. Angew. Chem., Int. Ed. 1987, 26, 267
19. Boysen, M. Chem.-Eur. J. 2007, 13, 8648
20. Wang, Y.; Yu, J.; Miao, Z.; Chen, R. Chem.-Eur. J. 2009, 15, 9290
21. King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089
22. Howland, J. L. Biochem. Educ. 1996, 24, 69
23. Totani, K.; Takao, K.; Tadano, K. Synlett 2004, 12, 2066
24. Banaag, A. R.; Tius, M. A. J. Org. Chem. 2008, 73, 8133
25. Moreno-Clavijo, E.; Carmona, A. T.; Reissig, H.-U.; Moreno-Vargas, A. J.; Alvarez, E.; Robina, I. Org. Lett. 2009, 11, 4778
26. Kaden, S.; Brockmann, M.; Reissig, H. U. Helv. Chim. Acta 2005, 88, 1826
27. Lorpitthaya, R.; Xie, Z. Z.; Sophy, K. B.; Luo, J. L.; Liu, X.-W. Chem.-Eur. J. 2010, 16, 588
28. Gorityala, B. K.; Cai, S.; Lorpitthaya, R.; Ma, J.; Pasunooti, K. K.; Liu, X.-W. Tetrahedron Lett. 2009, 50, 676
29. Lorpitthaya, R.; Sophy, K. B.; Kuo, J. L.; Liu, X.-W. Org. Biomol. Chem. 2009, 7, 1284
30. Vedachalam, S.; Zeng, J.; Gorityala, B. K.; Antonio, M.; Liu, X.-W. Org. Lett. 2009, 12, 352
31. Liu, X.-W.; Le, T. N.; Lu, Y. P.; Xiao, Y. J.; Ma, J. M.; Li, X. Org. Biomol. Chem. 2008, 6, 3997
32. Cheng, X.-M.; Liu, X.-W. J. Comb. Chem. 2007, 9, 906
33. Banaag, A. R.; Tius, M. A. J. Am. Chem. Soc. 2007, 129, 5328
34. 3 (0.2 equiv), and the mixture was stirred for 30 min at 60 °C. The mixture was filtered, evaporated, and purified by column chromatography to afford compound 3a (see Supporting Information).
35. Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132
36. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
37. Gung, B.; Craft, D.; Bailey, L.; Kirschbaum, K. Chem.-Eur. J. 2010, 16, 639
38. Yamashita, Y.; Guo, X.-X.; Takashita, R.; Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 3262
39. Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720
40. Huang, P.-Q.; Wu, T.-J.; Ruan, Y.-P. Org. Lett. 2003, 5, 4341
41. Gante, J. Angew. Chem., Int. Ed. 1994, 33, 1699