Stereoselective 6-exo cyclization of amidyl radicals. An experimental and theoretical study

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8100-8106

  Zhuang, Shunjun ^a   Liu, Kun ^b   Li, Chaozhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b TIANJIN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDYL RADICALS; CYCLIZATION REACTIONS; STEREO-SELECTIVE; THEORETICAL STUDY; TRANSITION STATE;

AMIDES; STEREOSELECTIVITY;

CYCLIZATION;

AMIDYL RADICAL; DELTA LACTAM; LACTAM; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; EXPERIMENTAL STUDY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THEORETICAL STUDY;

AMIDES; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 80054115035     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2014406     Document Type: Article

References (50)

1. see:(a) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350.
2. (b) Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1993; Vol. 58, pp 1-45.
3. (c) Zard, S. Z. Synlett 1996, 1148-1154.
4. (d) Fallis, A. G.; Brinza, I.M. Tetrahedron 1997, 53, 17543-17594.
5. (e) Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 407-424.
6. (f) Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603-1618.
7. see:(a) Sutcliffe, R.; Ingold, K. U. J. Am. Chem. Soc. 1982, 104, 6071-6075.
8. (b) Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1993, 34, 6877-6880.
9. (c) Horner, J. H.; Musa, O. M.; Bouvier, A.; Newcomb, M. J. Am. Chem. Soc. 1998, 120, 7738-7748.
10. (d) Martinez, E.; Newcomb, M. J. Org. Chem. 2006, 71, 557-561.
11. (a) Guin, J.; Mück-Lichtenfeld, C.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2007, 129, 4498-4503.
12. (b) Kemper, J.; Studer, A. Angew. Chem., Int. Ed. 2005, 44, 4914-4917.
13. (c) Walton, J. C.; Studer, A. Acc. Chem. Res. 2005, 38, 794-802.
14. (a) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H.-S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. 1999, 38, 1669-1675.
15. (b) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625-628.
16. (c) Nicolaou, K. C.; Baran, P. S.; Kranich, R.; Zhong, Y.-L.; Sugita, K.; Zou, N. Angew. Chem., Int. Ed. 2001, 40, 202-206.
17. (d) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233-2244.
18. Janza, B.; Studer, A. J. Org. Chem. 2005, 70, 6991-6994.
19. Gagosz, F.; Moutrille, C.; Zard, S. Z. Org. Lett. 2002, 4, 2707-2709.
20. Gaudreault, P.; Drouin, C.; Lessard, J. Can. J. Chem. 2005, 83, 543-545.
21. Clark, A. J.; Fullaway, D. R.; Murphy, N. P.; Parekh, H. Synlett 2010, 610-614.
22. (a) Tang, Y.; Li, C. Org. Lett. 2004, 6, 3229-3231.
23. (b) Lu, H.; Li, C. Tetrahedron Lett. 2005, 46, 5983-5985.
24. (c) Chen, Q.; Shen, M.; Tang, Y.; Li, C. Org. Lett. 2005, 7, 1625-1627.
25. (d) Hu, T.; Shen, M.; Chen, Q.; Li, C. Org. Lett. 2006, 8, 2647-2650.
26. (e) Yuan, X.; Liu, K.; Li, C. J. Org. Chem. 2008, 73, 6166-6171.
27. (a) Biechy, A.; Hachisu, S.; Quiclet-Sire, B.; Ricard, L.; Zard, S. Z. Tetrahedron 2009, 65, 6730-6738.
28. (b) Biechy, A.; Hachisu, S.; Quiclet-Sire, B.; Ricard, L.; Zard, S. Z. Angew. Chem., Int. Ed. 2008, 47, 1436-1438.
29. (c) Callier-Dublanchet, A.-C.; Cassayre, J.; Gagosz, F.; Quiclet-Sire, B.; Sharp, L. A.; Zard, S. Z. Tetrahedron 2008, 64, 4803-4816.
30. (d) Sharp, L.; Zard, S. Z. Org. Lett. 2006, 8, 831-834.
31. (e) Cassayre, J.; Gagosz, F.; Zard, S. Z. Angew. Chem., Int. Ed. 2002, 41, 1783-1785.
32. (a) Clark, A. J.; Peacock, J. L. Tetrahedron Lett. 1998, 39, 6029-6032.
33. (b) Clark, A. J.; Deeth, R. J.; Wongtap, H. Synlett 1999, 444-446.
34. Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181-190.
35. see:(a) Martín, Á.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2005, 7, 2027-2030.
36. (b) Reddy, L. R.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2006, 8, 2819-2821.
37. (c) Francisco, C. G.; Herrera, A. J.; Martín, Á.; Pérez-Martín, I.; Suárez, E. Tetrahedron Lett. 2007, 48, 6384-6388.
38. (d) Chen, K.; Richter, J. M.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 7247-7249.
39. Hu, T.; Liu, K.; Shen, M.; Yuan, X.; Tang, Y.; Li, C. J. Org. Chem. 2007, 72, 8555-8558.
40. (a) Lu, H.; Chen, Q.; Li, C. J. Org. Chem. 2007, 72, 2564-2569.
41. (b) Liu, F.; Liu, K.; Yuan, X.; Li, C. J. Org. Chem. 2007, 72, 10231-10234.
42. Coleman, R. S.; Garg, R. Org. Lett. 2001, 3, 3487-3490.
43. Amans, D.; Bellosta, V.; Cossy, J. Org. Lett. 2007, 9, 4761-4764.
44. see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
45. Yorimitsu, H.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2001, 74, 225-235.
46. Frisch, M. J. Gaussian 09, revision A.02; Gaussian Inc.: Wallingford, CT, 2009. See the Supporting Information for the full reference.
47. see: Schiesser, C.H.; Skidmore, M. A. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, pp 337-359.
48. See: Hanessian, S.; Dhanoa, D. S.; Beaulieu, P. L. Can. J. Chem. 1987, 65, 1859-1866.
49. see:(a) Zhai, H.; Zlotorzynska, M.; Sammis, G. M. Chem. Commun. 2009, 5716-5718.
50. (b) Zlotorzynska, M.; Zhai, H.; Sammis, G. M. J. Org. Chem. 2010, 75, 864-872