Multicomponent synthesis of highly substituted imidazolines via a silicon mediated 1,3-dipolar cycloaddition

Synthesis

Volumn , Issue 9, 2003, Pages 1433-1440

  Peddibhotla, S ^a   Tepe, J J ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

1,3 dipolar cycloaddition; Diastereoselective; Heterocycles; Imidazoles; Imidazolines

Indexed keywords

ADDITION REACTIONS; NITROGEN COMPOUNDS; SILICON; SUBSTITUTION REACTIONS;

CYCLOADDITION REACTIONS;

SYNTHESIS (CHEMICAL);

IMIDAZOLINE DERIVATIVE; SILICON;

ARTICLE; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0038236534     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40196     Document Type: Article

References (36)

1. Vedejs, E. Advances in Cycloaddition; JAI: Greenwich CT, 1988.
2. Padwa, A.; Schoffstall, A. M. Advances in Cycloaddition 1990, 2, 1.
3. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984, Vols. 1 & 2.
4. Harwood, L. M.; Vickers, R. J. Chem. Heterocycl. Compd. 2002, 59, 169.
5. Synthetic Applications of Dipolar Cycloaddition Chemistry Towards Heterocyclic and Natural Products; Padwa, A.; Pearson, W., Eds.; Wiley-VCH: Weinheim, 2002.
6. Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27, 981.
7. Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400.
8. Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2002, 42, 4236.
9. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
10. Gothelf, K. V.; Jensen, K. B.; Jorgensen, K. A. Sci. Prog. 1999, 82, 327.
11. Padwa, A.; Burgess, E. M.; Gingrich, H. L.; Roush, D. M. J. Org. Chem. 1982, 47, 786.
12. Consonni, R.; Croce, P. D.; Ferraccioli, R.; La Rosa, C. J. Chem. Res., Synop. 1991, 188.
13. Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800.
14. Gotthardt, H.; Huisgen, R.; Bayer, H. O. J. Am. Chem. Soc. 1970, 92, 4340.
15. Croce, P. D.; Ferraccioli, R.; La Rosa, C. Tetrahedron 1999, 55, 201.
16. Peddibhotla, S.; Jayakumar, S.; Tepe, J. J. Org. Lett. 2002, 4, 3533.
17. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580.
18. Perry, M. C.; Burges, K. Tetrahedron: Asymmetry 2003, 14, 951.
19. Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
20. Alexakis, A.; Winn, C. L.; Guillen, F.; Pytkowicz, J.; Roland, S.; Mangeney, P. Adv. Synth. Catal. 2003, 345, 345.
21. Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron: Asymmetry 2001, 12, 2083.
22. Gilbert, I. H.; Rees, D. C. Tetrahedron 1995, 51, 6315.
23. Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586.
24. Puntener, K.; Hellman, M. D.; Kuester, E.; Hegedus, L. S. J. Org. Chem. 2000, 65, 8301.
25. Boland, N. A.; Casey, M.; Hynes, S. J.; Matthews, J. W.; Smyth, M. P. J. Org. Chem. 2002, 67, 3919.
26. Derstine, C. W.; Smith, D. N.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1996, 118, 8485.
27. Dghaym, R. D.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. Engl. 2001, 40, 3228.
28. Dhawan, R.; Dghaym, R. D.; Arndtsen, B. A. J. Am. Chem. Soc. 2003, 125, 1474.
29. Mukerjee, A. K. Heterocycles 1987, 26, 1077.
30. Avalos, M.; Babiano, R.; Cintas, P.; Hursthouse, M. B.; Jimenez, J. L.; Light, M. E.; Lopez, I.; Palacios, J. C.; Silvero, G. Chemistry 2001, 7, 3033.
31. Prasad, K. K.; Petrzilka, T. Helv. Chim. Acta 1975, 58, 2504.
32. Chen, F. M. F.; Kuroda, K.; Benoiton, N. L. Synthesis 1979, 230.
33. Viso, A.; Fernandez De La Pradilla, R.; Guerrero-Strachan, C.; Alonso, M.; Martinez-Ripoll, M.; Andre, I. I. J. Org. Chem. 1997, 62, 2316.
34. Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. Tetrahedron 2003, 59, 197.
35. Komatsu, M.; Okada, H.; Yokoi, S.; Minakata, S. Tetrahedron Lett. 2003, 44, 1603.
36. Komatsu, M.; Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S. Org. Lett. 2002, 4, 3505.