The Cp2TiPh-mediated reductive radical cyclization of cyanoketones and related reactions. Efficient trapping of ketyl radicals by Cp2TiPh- coordinated polar multiple bonds

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3224-3229

  Yamamoto, Yoshihiko ^a   Matsumi, Daisuke ^a   Hattori, Reiko ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYCYCLOPENTANONE; ALKANONE; CYANOKETONE; KETOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 0033617460     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982492s     Document Type: Article

References (46)

1. (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, Chapter 4.
2. (b) Surzur, J.-M. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1982; Vol. 2, Chapter 3.
3. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, Chapters 4.2.2 and 4.2.3.
4. (d) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995.
5. (e) Curran, D. P. Synthesis 1988, 417, 489.
6. (f) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995.
7. (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
8. (b) Koert, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 405.
9. Yamamoto, Y.; Matsumi, D.; Itoh, K. Chem. Commun. 1998, 875.
10. (a) Hanada, Y.; Inanaga, J. Tetrahedron Lett. 1987, 46, 5717.
11. (b) Schobert, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 855.
12. (c) Gansäuer, A. J. Chem. Soc., Chem. Commun. 1997, 457.
13. (d) Gansäuer, A. Synlett 1997, 363.
14. (e) Gansäuer, A.; Bauer, D. J. Org. Chem. 1998, 63, 2070.
15. (f) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
16. (g) de Boer, E. J. M.; Teuben, J. H. J. Organomet. Chem. 1977, 140, 41.
17. (h) de Boer, E. J. M.; Teuben, J. H. J. Organomet. Chem. 1978, 153, 53.
18. (i) Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561.
19. (j) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1989, 111, 4525.
20. (k) RajanBabu, T. V.; Nugent, W. A.; Beattie, M. S. J. Am. Chem. Soc. 1990, 112, 6408.
21. (l) Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849.
22. (m) Yadav, J. S.; Srinivas, D. Chem. Lett. 1997, 905.
23. (n) Chakraborty, T. K.; Dutta, S. J. Chem. Soc., Perkin Trans. 1 1997, 1257.
24. (o) Davies, S. G.; Thomas, S. E. Synthesis 1984, 1027.
25. (p) Yanlong, Q.; Guisheng, L.; Huang, Y.-Z. J. Organomet. Chem. 1990, 381, 29.
26. (q) Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204.
27. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
28. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
29. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
30. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
31. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
32. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
33. For radical addition of imidoyl radicals, see: (a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. (b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. (c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757. (d) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886. (e) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127. (f) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (f) Bachi, M. D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.
34. 2TiPh was used to ensure the completion of reaction.
35. 3) were optimized at the unrestricted Hartree-Fock (UHF) level with a PM3 Hamiltonian (Stewart, J. J. R. J. Comput.-Aided Mol. Des. 1990, 4, 1).
36. For radical cyclization involving a nitrile group, see: (a) Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313. (b) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409. (c) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116. (d) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322. (also see refs 9-11).
37. For radical cyclization involving a nitrile group, see: (a) Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313. (b) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409. (c) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116. (d) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322. (also see refs 9-11).
38. For radical cyclization involving a nitrile group, see: (a) Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313. (b) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409. (c) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116. (d) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322. (also see refs 9-11).
39. For radical cyclization involving a nitrile group, see: (a) Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313. (b) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409. (c) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116. (d) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322. (also see refs 9-11).
40. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
41. Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
42. Shono, T.; Kise, N.; Fujimoto, T.; Tominaga, N.; Morita, H. J. Org. Chem. 1992, 57, 7175.
43. Waters, J. A.; Mortimer, G. A. J. Organomet. Chem. 1970, 22, 417.
44. The reductive cyclization of ketoester 12c in Na/ammonia was reported to give a mixture of products given below (Gutsche, G. D.; Tao, I. Y. C.; Kozma, J. J. Org. Chem. 1967, 32, 1782.). equation presented
45. 2 (Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063).
46. Syper, L. Tetrahedron 1987, 43, 2853.