Stereoselective synthesis of 5-substituted pyrrolo[1,2-c]imidazol-3-ones: Access to annulated chiral imidazol(in)ium salts

Organic Letters

Volumn 12, Issue 1, 2010, Pages 76-79

  Metallinos, Costa ^a   Xu, Shufen ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; INORGANIC SALT; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; IMIDAZOLES; MOLECULAR STRUCTURE; PYRROLES; SALTS; STEREOISOMERISM;

EID: 73949122156     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902277y     Document Type: Article

References (46)

1. Huang, J.-M.; Hong, S.-C.; Wu, K.-L.; Tsai, T.-M. Tetrahedron Lett. 2004, 45, 3047, and references therein.
2. (a) Fontaneila, L.; Corsico, N.; Diena, A.; Occelli, E. Farmaco, Ed. Sci. 1984, 39, 133.
3. (b) Fontanella, L.; Occelli, E.; Perazzi, A. Farmaco, Ed. Sci. 1973, 28, 463.
4. (c)Fontaneila, L.; Occelli, E. Farmaco, Ed. Sci. 1971, 26, 685.
5. (a) Ksander, G. M.; Meredith, E.; Monovich, L. H.; Papillon, J.; Firooznia, F.; Hu, Q. WO 024945 (2007).
6. (b) Browne, L. J.; Gude, C.; Rodriguez, H.; Steele, R. E. J. Med. Chem. 1991, 34, 725.
7. Isobe, T.; Fukuda, K.; Ishikawa, T. J. Org. Chem. 2000, 65, 7770.
8. (a) DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10872.
9. (b) Rovis, T. Chem. Lett. 2008, 37, 2.
10. (c)de Alaniz, J. R.; Kerr, M. S.; Moore, J. L.; Rovis, T. J. Org. Chem. 2008, 73, 2033.
11. (d)Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
12. (e) Christmann, M. Angew. Chem., Int. Ed. 2005, 44, 2632.
13. (f) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951.
14. (g) He, L.; Zhang, Y.-R.; Huang, X.-L.; Ye, S. Synthesis 2008, 2825.
15. (a) Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691.
16. (b) Nair, V.; Babu, B. P; Vellalath, S.; Varghese, V.; Raveendran, A. E.; Suresh, E. Org. Lett. 2009, 11, 2507.
17. (c)Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736.
18. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
19. (a) Struble, J. R.; Kaeobamrung, J.; Bode, J. W. Org. Lett. 2008, 10, 957.
20. (b) Struble, J. R.; Bode, J. W. Tetrahedron 2008, 64, 6961. Review:
21. (c)Arduengo, A. J.; Iconaru, L. I. Dalton Trans. 2009, 6903.
22. (a)For α-chiral annulated NHCs in transition metal catalysis, see: (a) Metallinos, C.; Du, X. Organometallics 2009, 28, 1233.
23. (b) Metallinos, C.; Barrett, F. B.; Wang, Y.; Xu, S.; Taylor, N. J. Tetrahedron 2006, 62, 11145.
24. (c)Würtz, S.; Lohre, C.; Fröhlich, R.; Bergander, K.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 8344.
25. (d)Glorius, F.; Altenhoff, G.; Goddard, R.; Lehmann, C. Chem. Commun. 2002, 2704.
26. (e) Baskakov, D.; Herrmann, W. A.; Herdtweck, E.; Hoffmann, S. D. Organometallics 2007, 26, 626.
27. Metallinos, C.; Dudding, T; Zaifman, J.; Chaytor, J. L.; Taylor, N. J. J. Org. Chem. 2007, 72, 957.
28. (a) Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
29. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
30. (c)Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. 1997, 36, 2282.
31. (a) Stead, D.; O'Brien, P.; Sanderson, A. Org. Lett. 2008, 10, 1409.
32. (b) Mealey, M. J.; Luderer, M. R.; Bailey, W. F.; Sommer, M. B. J. Org. Chem. 2004, 69, 6042.
33. (c)O'Brien, P. Chem. Commun. 2008, 655.
34. (a) Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-Y. J. Am. Chem. Soc. 2006, 128, 3538.
35. (b) O'Brien, P.; Bilke, J. L. Angew. Chem., Int. Ed. 2008, 47, 2734.
36. Bertini Gross, K. M.; Beak, P. J. Am. Chem. Soc. 2001, 123, 315.
37. (a) Corma, A.; Iglesias, M.; del Pino, C.; Sánchez, F. J. Organomet. Chem. 1992, 431, 233.
38. (b) Corey, E. J.; Saizo, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861.
39. Compound 17 was minimized at the B3LYP/6-31G(d) level as implemented in Gaussian 03.
40. 13C NMR chemical shift of 18.2 ppm compared to 22.5 ppm in anti-20b. The difference in resonance frequency can be attributed to a γ-effect and may be used to assign syn and anti streochemistry in these ureas and related chiral bicyclic ketones with a high degree of confidence. See: (a) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P J. Org. Chem. 1980, 45, 5020.
41. (b) Hudlicky, T.; Koszyk, F. J.; Dochwat, D. M.; Cantrell, G. L. J. Org. Chem. 1981, 46, 2911.
42. Review: Crouch, D. R. Tetrahedron 2009, 65, 2387.
43. Snead, D. R.; Ghiviriga, I.; Abboud, K. A.; Hong, S. Org. Lett. 2009, 11, 3274.
44. (a) Chase, P. A.; Stephan, D. W. Angew. Chem., Int. Ed. 2008, 47, 7433.
45. (b) Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem., Int. Ed. 2008, 47, 7428.
46. Wen, Y.; Zhao, B.; Shi, Y. Org. Lett. 2009, 11, 2365.