Transition-Metal-Centered Radicals in Organic Synthesis. Titanium(III)-Induced Cyclization of Epoxyolefins

Journal of the American Chemical Society

Volumn 110, Issue 25, 1988, Pages 8561-8562

  Nugent, William A ^a   RajanBabu, T V ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845280764     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00233a051     Document Type: Article

References (8)

1. Julia, M. Pure Appl. Chem. 1974, 40, 553–567. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073–3100. Burnett, D. A.; Choi, J.; Hart, D. J.; Tsai, Y. J. Am. Chem. Soc. 1984, 106, 8201–8209. Curran, D. P.; Kuo, S. J. Am. Chem. Soc. 1986, 108, 1106–1107. Stork, G.; Sher, P. M.; Chen, H.-L. J. Am. Chem. Soc. 1986, 108, 6384–6385. RajanBabu, T. V. J. Org. Chem. 1988, 53, 4522–4530.
2. Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489–2490.
3. Begley, M. J.; Bhandal, H.; Hutchinson, J. H.; Pattenden, G. Tetrahedron Lett. 1987, 28, 1317–1320. See, also: Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303–304.
4. 4bwas the first of several workers to propose that some of these reactions may proceed by discrete one-electron steps via the carbon-centered radical, (a) For a review, see: Wong, H. C.; Fok, C. C. M.; Wong, T. Heterocycles 1987, 26, 1345–1382. (b) Kochi, J. K.; Singleton, D. M.; Andrews, L. J. Tetrahedron 1968, 24, 3503–3515.
5. 2) gives comparable yields (Table I). (a) Manzer, L. E. Inorg. Synth. 1982, 21, 84–86. (b) Green, M. L. H.; Lucas, C. R. J. Chem. Soc., Dalton Trans. 1972, 1000–1003.
6. Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811–2814.
7. Other radical routes from carbohydrates to chiral cyclopentanes: Wilcox, C. S.; Gaudino, J. J. J. Am. Chem. Soc. 1986, 108, 3102–3104. RajanBabu, T. V. J. Am. Chem. Soc. 1987, 109, 609–611.
8. 2, promotes an unprecedented dimerization of silylimines and nitriles to vicinal diamines. However, they note that 5-hexenenitrile is not cyclized suggesting that there is no long-lived carbon radical associated with the system: Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152–3154.