Organocatalytic enantioselective aza-Friedel-crafts alkylation of pyrroles with N-(heteroarenesulfonyl)imines

Synlett

Volumn , Issue 10, 2009, Pages 1639-1642

  Nakamura, Shuichi ^a   Sakurai, Yuki ^a   Nakashima, Hiroki ^a   Shibata, Norio ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Amines; Asymmetric synthesis; Aza Friedel crafts alkylation; Heteroarylsulfonyl group; Organocatalysis

Indexed keywords

HETEROCYCLIC COMPOUND; IMINE; NAPHTHOL DERIVATIVE; PHOSPHORIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 67649344302     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217324     Document Type: Article

References (49)

1. (a) Della Bella, D. Boll. Chim. Farm. 1972, 111, 5.
2. (b) Guzman, A.; Yuste, F.; Toscano, R. A.; Young, J. M.; Vanhorn, A. R.; Muchowski, J. M. J. Med. Chem. 1986, 29, 589.
3. (c) Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 4th ed.; Thieme: New York, 2001.
4. (d) Katritzky, A. R.; Jain, R.; Xu, Y.; Steel, P. J. J. Org. Chem. 2002, 67, 8220.
5. For recent reviews on asymmetric Friedel-Crafts alkylations using chiral Lewis acids, see: (a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem. Int. Ed. 2004, 43, 550.
6. (b) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
7. (a) Johannsen, M. Chem. Commun. 1999, 2233.
8. (b) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 4114.
9. (c) Saaby, S.; Bayón, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352.
10. (d) Jia, Y.-X.; Xie, J.-H.; Duan, H.-F.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2006, 8, 1621.
11. (a) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
12. (b) Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
13. (c) Terada, M.; Yokoyama, S.; Sorimachi, K.; Uraguchi, D. Adv. Synth. Catal. 2007, 349, 1863.
14. (d) Kang, Q.; Zhao, Z.; You, S. J. Am. Chem. Soc. 2007, 129, 1484.
15. (e) Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J. A.; Antilla, J. C. Org. Lett. 2007, 9, 2609.
16. (f) Zhang, G.-W.; Wang, L.; Nie, J.; Ma, J.-A. Adv. Synth. Catal. 2008, 350, 1457.
17. (g) Kang, Q.; Zhao, Z.-A.; You, S.-L. Tetrahedron 2009, 65, 1603.
18. For enantioselective aza-Friedel - Crafts reactions to enecarbamates, see: (h) Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292.
19. (i) Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2007, 46, 5565.
20. For asymmetric Pictet-Spengler cyclization, see: (j) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
21. (k) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
22. (l) Wanner, M. J.; van der Hass, R. N. S.; de Cuba, K. R.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem. Int. Ed. 2007, 46, 7485.
23. Li, G.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C. Org. Lett. 2007, 9, 4065.
24. Kang, Q.; Zheng, X.-J.; You, S.-L. Chem. Eur. J. 2008, 14, 3539.
25. (a) Nakamura, S.; Sato, N.; Sugimoto, M.; Toru, T. Tetrahedron: Asymmetry 2004, 15, 1513.
26. (b) Sugimoto, H.; Nakamura, S.; Hattori, M.; Ozeki, S.; Shibata, N.; Toru, T. Tetrahedron Lett. 2005, 46, 8941.
27. (c) Nakamura, S.; Nakashima, H.; Sugimoto, H.; Shibata, N.; Toru, T. Tetrahedron Lett. 2006, 47, 7599.
28. (d) Nakamura, S.; Sano, H.; Nakashima, H.; Kubo, K.; Shibata, N.; Toru, T. Tetrahedron Lett. 2007, 48, 5565.
29. (e) Nakamura, S.; Nakashima, H.; Sugimoto, H.; Sano, H.; Hattori, M.; Shibata, N.; Toru, T. Chem. Eur. J. 2008, 14, 2145.
30. (f) Esquivias, J.; Arrayás, R. G.; Carretero, J. C. J. Org. Chem. 2005, 70, 7451.
31. (g) Llamas, T.; Arrayás, R. G.; Carretero, J. C. Angew. Chem. Int. Ed. 2007, 46, 3329.
32. (h) Llamas, T.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 1795.
33. (i) Esquivias, J.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 1480.
34. (j) González, A. S.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 2977.
35. (k) Morimoto, H.; Lu, G.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 9588.
36. (l) Lu, G.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Angew. Chem. Int. Ed. 2008, 47, 6847.
37. (m) González, A. S.; Arrayás, R. G.; Rivero, M. R.; Carretero, J. C. Org. Lett. 2008, 10, 4335.
38. (n) Esquivias, J.; Alonso, I.; Arrayás, R. G.; Carretero, J. C. Synthesis 2009, 113.
39. (a) Nakamura, S.; Nakashima, H.; Yamamura, A.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1209.
40. (b) Nakamura, S.; Hara, N.; Nakashima, H.; Kubo, K.; Shibata, N.; Toru, T. Chem. Eur. J. 2008, 14, 8079.
41. 2-(±)-BINAP], see: (a) Alonso, I.; Esquivias, J.; Gómez-Arrayás, R.; Carretero, J. C. Angew. Chem. Int. Ed. 2006, 45, 629.
42. (b) Alonso, I.; Esquivias, J.; Gómez-Arrayás, R.; Carretero, J. C. J. Org. Chem. 2008, 73, 6401.
43. For reviews, see: (a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
44. (b) Terada, M. Chem. Commun. 2008, 4097; and references therein.
45. For reviews, see: (a) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
46. (b) Miyabe, H.; Takamoto, Y. Bull. Chem. Soc. Jpn. 2008, 81, 785; and references therein.
47. We also examined several chiral Lewis acids, such as Box- Mg(II), Box-Cu(II), and BINAP-Pd(II), giving the product 2a in low yield.
48. 2O, EtOH, and MeCN, using 3b giving the product 2a with lower enantioselectivity than that in toluene.
49. Unfortunately, aliphatic N-(2-pyridylsulfonyl)imines could not be obtained from aliphatic aldehydes under various reaction conditions.