Ti(III)-catalyzed radical cyclization of 6,7-epoxygeranyl acetate

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1961-1963

  Fuse, Shinichiro ^a   Hanochi, Malcoln ^a   Doi, Takayuki ^a   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GERANYL ACETATE; TITANIUM;

ARTICLE; CATALYSIS; CYCLIZATION; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 1242293806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.138     Document Type: Article

References (14)

1. RajanBabu T.V., Nugent W.A. J. Am. Chem. Soc. 116:1994;986-997.
2. Nugent W.A., RajanBabu T.V. J. Am. Chem. Soc. 110:1988;8561-8562.
3. RajanBabu T.V., Nugent W.A. J. Am. Chem. Soc. 111:1989;4525-4527.
4. Barrero A.F., Cuerva J.M., Herrador M.M., Valdivia M.V. J. Org. Chem. 66:2001;4074-4078.
5. Nakai K., Kamoshita M., Doi T., Yamada H., Takahashi T. Tetrahedron Lett. 42:2001;7855-7857.
6. Nakai K., Miyamoto S., Sasuga D., Doi T., Takahashi T. Tetrahedron Lett. 42:2001;7859-7862.
7. Gansäuer A., Bluhm H., Pierobon M. J. Am. Chem. Soc. 120:1998;12849-12859.
8. Gansäuer A., Rinker B., Pierobon M., Grimme S., Gerenkamp M., Mück-Lichtenfeld C. Angew. Chem., Int. Ed. 42:2003;3687-3690.
9. Gansäuer A., Bluhm H., Rinker B., Narayan S., Schick M., Lauterbach T., Pierobon M. Chem. Eur. J. 9:2003;531-542.
10. Barrero A.F., Rosales A., Cuerva J.M., Oltra J.E. Org. Lett. 5:2003;1935-1938.
11. Fujita K., Nakamura T., Yorimitsu H., Oshima K. J. Am. Chem. Soc. 123:2001;3137-3138.
12. As a referee pointed out, it is not obvious whether the transformation of 2 to 3 is faster than the disproportionation of 2 forming a double bond. However, considering that the addition of pyridinium salts is more effective than that of triethylborane to accelerate the catalytic system, we assume that the transformation of 2 to 3 is faster than the disproportionation.
13. Fürstner A., Shi N. J. Am. Chem. Soc. 118:1996;2533-2534.
14. Fürstner A., Shi N. J. Am. Chem. Soc. 118:1996;12349-12357.