Optimizing the 5-exo/6-endo ratio of vinyl radical cyclizations through catalysis with diphenyl diselenide

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3105-3108

  Crich, David ^a   Hwang, Jae Taeg ^a   Liu, Hui ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029928046     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00526-6     Document Type: Article

References (20)

1. Stork, G.; Baine, N. H. J. Am. Chem. Soc. 1982, 104, 2321.
2. (a) Motherwell, W. B.; Crich, D. 'Free Radical Chain Reactions in Organic Synthesis', Academic Press, London, 1992.
3. (b) Curran, D. P. Synthesis 1988, 417 and 489.
4. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
5. Nishida, M.; Nobuta, M. Tetrahedron: Asymmetry 1995, 6, 2657.
6. (a) Beckwith, A. L. J.; O'Shea, D. M. Tetrahedron Lett. 1986, 27, 4525.
7. (b) Stork, G.; Mook, R. Tetrahedron Lett. 1986, 27, 4529.
8. (a) Allen, R. P.; Roberts, B. P.; Willis, C. R. J. Chem. Soc., Chem. Commun., 1989, 1387.
9. (b) Cole, S. J.; Kirwan, J. N.; Roberts, B. P.; Willis, C. R. J. Chem. Soc., Perkin Trans. I 1991, 103.
10. (c) Also see: Yeung, D. W. Y.; Warkentin, J. Can. J. Chem. 1976, 54, 1345.
11. For an alternative explanation of the catalytic effects of thiols and selenols in radical chain reactions see: Zavitsas, A.; Chatgilialoglu, C. J. Am. Chem. Soc. 1995, 117, 10645.
12. Crich, D.; Yao, Q. J. Org. Chem. 1995, 60, 84.
13. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739.
14. Newcomb, M.; Variek, T. K.; Ha, C.; Manek, M. B.; Yue, X. J. Am. Chem. Soc. 1992, 114, 8158.
15. We thank Professor D. P. Curran, Pittsburgh, for this suggestion.
16. 7
17. Vinyl iodides 5 and 10 were prepared by standard alkylations of diethyl allylmalonate and N-allylbenz-enesulfonamide, respectively, with the mesylate of 2-iodo-2-propenol which in turn was prepared by standard mesylation of 2-iodo-2-propenol (eg Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett. 1990, 675)
18. Padwa, A.; Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
19. 14 A different ratio (12:13 = 3:1) is given in the text, but with no details of conditions.
20. As suggested by Stork, the 16:17 ratio was determined after oxidation to the corresponding ketones, although we oxidized with TPAP/NMNO (Ley, S. V.; Norman, J.; Griffith, W. P. Synthesis 1994, 639). No attempt was made to determine stereochemistry of 16 or 17 or of the ketones.