A Model Study of Intramolecular Asymmetric Radical Cyclizations of a-Ester and α-Amide Radicals

Journal of the Chinese Chemical Society

Volumn 44, Issue 3, 1997, Pages 253-260

  Yeh, Ru Long ^a   Jiaang, Weir Torn ^a   Tsai, Yeun Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

8 Phenylmenthol; Asymmetric radical; Chiral auxiliary; Radical cyclization; Tributyltin hydride; Amide radical; Ester radical

Indexed keywords

EID: 0003745708     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.199700039     Document Type: Article

References (29)

1. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
2. Chen, M.-Y.; Fang, J.-M.; Tsai, Y.-M.; Yeh, R.-L. J. Chem. Soc. Chem. Commun. 1991, 1603.
3. Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296.
4. Smadja, W. Synlett 1994, 1.
5. Snider, B. B. Chem. Rev. 1996, 96, 339.
6. For example, see: Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205.
7. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org Chem. 1990, 55, 5181.
8. For example, see: Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
9. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992, chap 7.
10. (a) Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943.
11. (b) Posner, G. H.; Asirvatham, E.; Hamill, T. G.; Webb, K. S. J. Org. Chem. 1990, 55, 2132.
12. (c) Renaud, P.; Schubert, S. Synlett 1990, 624.
13. (d) Beckwith, A. L. J.; Chai, C. L. L. Tetrahedron, 1993, 49, 7871.
14. (e) Sato, T.; Chono, N.; Ishibashi, H.; Ikeda, M. J. Chem. Soc. Perkin Trans. I, 1995, 1115.
15. For the use of α-phenylselenenyl esters or amides, see: (a) Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457. (b) Radinov, R.; Mero, C. L.; McPhail, A. T.; Porter, N. A. Tetrahedron Lett. 1995, 36, 8183. For xanthates, see ref 2.
16. For the use of α-phenylselenenyl esters or amides, see: (a) Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457. (b) Radinov, R.; Mero, C. L.; McPhail, A. T.; Porter, N. A. Tetrahedron Lett. 1995, 36, 8183. For xanthates, see ref 2.
17. Kwiatkowski, S.; Syed, A.; Brock, C.; Watt, D. S. Synthesis 1989, 818.
18. Ort, O. Org. Syn. 1987, 65, 203.
19. Yan, T-H.; Tan, C.-W.; Lee, H.-C.; Lo, H.-C.; Huang, T.-Y. J. Am. Chem. Soc. 1993, 115, 2613.
20. Brown, H. C.; Naik, R. G.; Bakshi, R. K.; Pyun, C.; Singaram, B. J. Org. Chem. 1985, 50, 5586.
21. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986, chap 4.
22. (a) Hamon, D. P. G.; Razzino, P.; Massy-Westropp, R. A. J. Chem. Soc. Chem. Commun. 1991, 332.
23. (b) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. J. Chem. Soc. Chem. Commun. 1991, 722.
24. (c) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron, 1993, 49, 6419.
25. (d) Snider, B. B.; Zhang, Q. Tetrahedron Lett. 1992, 33, 5921.
26. (e) Zhang, Q.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B. J. Org. Chem. 1993, 58, 7640.
27. Oppolzer, W.; Kurth, M.; Reichlin, D.; Chapuis, C.; Mohnhaupt, M.; Moffatt, F. Helv. Chim. Acta 1981, 64, 2802.
28. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983, chap 3.
29. Richter, W. J.; Richter, B. Israel J. Chem. 1976/77, 15, 57.