Stereospecificity in radical carbon-carbon bond formation reactions based on tartaric acid

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 23, 1987, Pages 1790-1792

  Barton, Derek H R ^a,b   Gateau Olesker, Alice ^a   Gero, Stephan D ^a   Lacher, Brigitte ^a   Tachdjian, Catherine ^a   Zard, Samir Z ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049082016     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39870001790     Document Type: Article

References (18)

1. D. Seebach and E. Hungerbuhler in ‘Modern Synthetic Methods,’ ed. E. Scheffold, Otto Salle Verlag, Frankfurt, 1980, and references therein.
2. H. J. Bestmann and T. Moenius, Angew. Chem., Int. Ed. Engl., 1986, 25, 994.
3. T. Kolasa and M. J. Miller, Tetrahedron Lett., 1987, 28, 1861.
4. A. Gateau-Olesker, J. Cléophax and S. D. Gero, Tetrahedron Lett., 1986, 27, 41.
5. F. Barrière, J.-C. Barrière, D. H. R. Barton, J. Cléophax, A. Gateau-Olesker, S. D. Gero, and F. Tadj, Tetrahedron Lett., 1985, 26, 3119, 3121.
6. W. R. Roush and A. D. Palkowitz, J. Am. Chem. Soc., 1987, 109, 953.
7. S. Takano, A. Kurotaki, Y. Sekiguchi, S. Satoh, M. Hirama and K. Ogasawara, Synthesis, 1986, 811.
8. B. Giese, ‘Radicals in Organic Synthesis: Formation of CarbonCarbon Bonds,’ Pergamon Press, 1986.
9. D. H. R. Barton and S. Z. Zard, Pure Appl. Chem., 1986, 58, 675.
10. A. L. J. Beckwith in ‘Free Radical Reactions,’ ed. W. A. Waters, M.T.P. International Review of Science, Vol. 10, Butterworths, London, 1973.
11. L. Kaplan in ‘Free Radicals,’ ed. J. K. Kochi, Vol. II, Wiley Interscience, 1973.
12. H. Walborsky, Tetrahedron, 1981, 37, 1625.
13. J. A. Musich and H. Rapoport, J. Am. Chem. Soc., 1978, 100, 48.
14. D. H. R. Barton, D. Bridon, Y. Hervé, P. Potier, J. Thierry, and S. Z. Zard, Tetrahedron, 1986, 42, 4983.
15. D. H. R. Barton, D. Crich, Y. Herve, P. Potier, and J. Thierry, Tetrahedron, 1985, 41, 4347.
16. The coupling constant we observe is closer to that of cis 2, 2, 4, 5- tetramethyl-l,3-dioxolane (5.85 Hz) than to that of the trans isomer (8.35 Hz); F. A. L. Anet, J. Am. Chem. Soc., 1962, 84, 747. However, the flexibility of the five-membered ring makes such comparisons unreliable.
17. D. H. R. Barton, H. Togo, and S. Z. Zard, Tetrahedron, 1985, 23, 5507.
18. Y. Tsuzuki, Bull. Chem. Soc. Jpn., 1935, 11, 362.