Cinchona-based sulfonamide organocatalysts: Concept, scope, and practical applications

Bulletin of the Korean Chemical Society

Volumn 35, Issue 6, 2014, Pages 1590-1600

  Bae, Han Yong ^a   Song, Choong Eui ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Aldol reaction; Asymmetric catalysis; Cinchona based sulfonamide; Desymmetrization; Textile organocatalysis

Indexed keywords

AGGREGATES; CATALYSIS; CONDENSATION REACTIONS; ENANTIOSELECTIVITY; HYDROGEN BONDS; METABOLISM; RATE CONSTANTS; REACTION KINETICS; SULFUR COMPOUNDS; UREA;

ALDOL REACTIONS; ASYMMETRIC CATALYSIS; CINCHONA-BASED SULFONAMIDE; DESYM-METRIZATION; ORGANOCATALYSIS;

CATALYSTS;

EID: 84902658556     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2014.35.6.1590     Document Type: Article

References (60)

1. Bredig, G.; Fiske, P. S. Bichem. Z 1912, 46, 7.
2. (a) Pracejus, H. Justus Liebigs Ann. Chem. 1960, 634, 9.
3. (b) Pracejus, H. Mätje. J. Prakt. Chem. 1964, 24, 195.
4. (a) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, 2005.
5. (b) Dalko, P. I. In Enantioselective Organocatalysis; Wiley-VCH: Weinheim, 2005.
6. (c) List, B. Chem. Rev. 2007, 107, 5413.
7. (d) Houk, K. N.; List, B. Acc. Chem. Res. 2004, 37, 487.
8. (e) List, B.; Yang, J. W. Science 2006, 313, 1584.
9. (f) MacMillan, D. W. C. Nature 2008, 455, 304.
10. (a) Song, C. E. Cinchona Alkaloids in Synthesis and Catalysis; Wiley-VCH: Weinheim, 2009.
11. (b) Marcelli, T.; Hiemstra, H. Synthesis 2010, 1229.
12. (a) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
13. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520.
14. (c) Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem. Int. Ed. 2006, 45, 7496.
15. (d) Connon, S. J. Chem. Eur. J. 2006, 12, 5418.
16. (e) Connon, S. J. Chem. Commun. 2008, 2499.
17. Vakulya, B.; Varga, S.; Csampai, A.; Soós, T. Org. Lett. 2005, 7, 1967.
18. Li, B. J.; Jiang, L.; Liu, M.; Chen, Y. C.; Ding, L. S.; Wu, Y. Synlett 2005, 603.
19. Malerich, J. P.; Hagihara, K.; Rawal, V. H. J. Am. Chem. Soc. 2008, 130, 14416.
20. Aleman, J.; Parra, A.; Jiang, H.; Jørgensen, K. A. Chem. Eur. J. 2011, 17, 6890.
21. Rho, H. S.; Oh, S. H.; Lee, J. W.; Lee, J. Y.; Chin, J.; Song, C. E. Chem. Commun. 2008, 1208.
22. (a) Tarkanyi, G.; Kiraly, P.; Varga, S.; Vakulya, B.; Soós, T. Chem. Eur. J. 2008, 14, 6078.
23. (b) Kiraly, P.; Soós, T.; Varga, S.; Vakulya, B.; Tarkanyi, G. Magn. Reson. Chem. 2010, 48, 13.
24. Honjo, T.; Sano, S.; Shiro, M.; Nagao, Y. Angew. Chem. Int. Ed. 2005, 44, 5838.
25. For recent reviews, see: (a) Atodiresei, L.; Schiffers, I.; Bolm, C. Chem. Rev. 2007, 107, 5683.
26. (b) de Villegas, M. D. D.; Galvez, J. A.; Etayo, P.; Badorrey, R.; Lopez-Ram-de-Viu, P. Chem. Soc. Rev. 2011, 40, 5564.
27. (c) Rodriguez-Docampo, Z.; Connon, S. J. Chemcatchem 2012, 4, 151.
28. Chen, Y. G.; Tian, S. K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542.
29. (a) Peschiulli, A.; Gun'ko, Y.; Connon, S. J. J. Org. Chem. 2008, 73, 2454.
30. (b) Peschiulli, A.; Quigley, C.; Tallon, S.; Gun'ko, Y. K.; Connon, S. J. J. Org. Chem. 2008, 73, 6409.
31. Jang, H. B.; Rho, H. S.; Oh, J. S.; Nam, E. H.; Park, S. E.; Bae, H. Y.; Song, C. E. Org. Biomol. Chem. 2010, 8, 3918.
32. For reviews on the stereoselective synthesis of γ-amino acids, see: (a) Trabocchi, A.; Menchi, G.; Guarna, A. Amino Acids, Peptides and Proteins in Organic Chemistry; Hughes, A. B., Ed.; Wiley-VCH: Weinheim, 2009; Vol. 1, Chapter 13.
33. (b) Hanrahan, J. R.; Johnston, G. A. R. Amino Acids, Peptides and Proteins in Organic Chemistry; Hughes, A. B., Ed.; Wiley-VCH: Weinheim, 2009; Vol. 1, Chapter 14.
34. (c) Ordonez, M.; Cativiela, C. Tetrahedron: Asymm. 2007, 18, 3.
35. (a) Liu, L. T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L. J.; Wen, Y.-S. Tetrahedron: Asymm. 2001, 12, 419.
36. (b) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647.
37. (a) Huang, X.; Zhu, J.; Broadbent, S. Tetrahedron Lett. 2010, 51, 1554.
38. (b) Huang, X.; O'Brien, E.; Thai, F.; Cooper, G. Org. Proc. Res. Dev. 2010, 14, 592.
39. Lim, K. PCT Int. Appl. WO 03/087112 A1.
40. Park, S. E.; Nam, E. H.; Bin Jang, H.; Oh, J. S.; Some, S.; Lee, Y. S.; Song, C. E. Adv. Synth. Catal. 2010, 352, 2211.
41. Youk, S. H.; Oh, S. H.; Rho, H. S.; Lee, J. E.; Lee, J. W.; Song, C. E. Chem. Commun. 2009, 2220.
42. Lee, J. W.; Mayer-Gall, T.; Opwis, K.; Song, C. E.; Gutmann, J. S.; List, B. Science 2013, 341, 1225.
43. Gerfaud, T.; Xie, C. S.; Neuville, L.; Zhu, J. P. Angew. Chem. Int. Ed. 2011, 50, 3954.
44. (a) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380.
45. (b) Shen, B. Curr. Opin. Chem. Biol. 2003, 7, 285.
46. (c) White, S. W.; Zheng, J.; Zhang, Y.-M.; Rock, C. O. Annu. Rev. Biochem. 2005, 74, 791.
47. (d) Hill, A. M. Nat. Prod. Rep. 2006, 23, 256.
48. (e) Smith, S.; Tsai, S.-C. Nat. Prod. Rep. 2007, 24, 1041.
49. (a) Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852.
50. (b) Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284.
51. (c) Fortner, K. C.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 1032.
52. For recent reviews, see: (a) Bernardi, L.; Fochi, M.; Comes Franchini, M.; Ricci, A. Org. Biomol. Chem. 2012, 10, 2911.
53. (b) Pan, Y.; Tan, C.-H. Synthesis 2011, 2011, 2044.
54. (c) Wang, Z.-L. Adv. Synth. Catal. 2013, 355, 2745.
55. (d) Nakamura, S. Org. Biomol. Chem. 2014, 12, 394.
56. Bae, H. Y.; Sim, J. H.; Lee, J.-W.; List, B.; Song, C. E. Angew. Chem. Int. Ed. 2013, 52, 12143.
57. Aldo, P.; Barbara, P.; Cornelius, J. O. C.; Stephen, J. C. Nat. Chem. 2010, 2, 380.
58. Luo, J.; Xu, L.-W.; Hay, R. A. S.; Lu, Y. Org. Lett. 2008, 11, 437.
59. Hara, N.; Nakamura, S.; Sano, M.; Tamura, R.; Funahashi, Y.; Shibata, N. Chem. Eur. J. 2012, 18, 9276.
60. Zhang, Y.; Xing, H.; Xie, W.; Wan, X.; Lai, Y.; Ma, D. Adv. Synth. Catal. 2013, 355, 68.