Formation of Cis-Fused Cyclopentanoids by Michael Addition and Radical Cyclization

Journal of Organic Chemistry

Volumn 54, Issue 8, 1989, Pages 1997-2003

  Clive, Derrick L J ^a   Clive Boivin, Taryn L B ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001058584     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00269a046     Document Type: Note

References (25)

1. See, e.g.: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1 and references therein.
2. Review: Ramaiah, M. Synthesis 1984, 529.
3. Curran, D. P. Synthesis 1988, 417 and 489. Hart D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986. Ramaiah, M. Tetrahedron 1987. 43. 3541.
4. Bartlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988,110, 1633. Barton, D. H. R.; da Silva, E.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1988, 285. Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984,49,1313. Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 980. Set, L.; Cheshire, D. R.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985,1205. Mohammed, A. Y.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1986, 588. Clive, D. L. J.; Cheshire, D. R.; Set, L. J. Chem. Soc., Chem. Commun. 1987 353. Clive, D. L. J.; Cheshire, D. R. J. Chem. Soc., Chem. Commun. 1987,1520. Clive, D. L. J.; Boivin, T. L. B.; Angoh, A. G. J. Org. Chem. 1987,52, 4943. (1) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985,107, 1448. (m) Chuang, C. P.; Gallucci, J. C.; Hart, D. J. J. Org. Chem. 1988, 53, 3210. (n) Chuang, C. P.; Gallucci, J. C.; Hart, D. J.; Hoffman, C. J. Org. Chem. 1988, 53, 3218. (o) Leonard, W. R.; Livinghouse, T. Tetrahedron Lett. 1985, 26, 6431. (p) Pattenden, G.; Robertson, G. M. Tetrahedron 1985, 41, 4001. (q) RajanBabu, T. V. J. Am. Chem. Soc. 1987, 109, 609. (r) Stork, G.; Baine, N. H. J. Am. Chem. Soc. 1982,104, 2321. (s) Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1983, 105, 3721. (t) Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1987, 109, 2829. (u) Wilcox, C. S.; Thomasco, L. M. J. Org. Chem. 1985, 50, 546. (v) Zeigler, F. E.; Zhong-li, Zheng Tetrahedron Lett. 1987, 28, 5973. (w) Yadav, V. K.; Fallis, A. G. Tetrahedron Lett. 1988, 29, 897.
5. Salomon, M. F.; Pardo, S. N.; Salomon, R. G. J. Org. Chem. 1984, 49, 2446. Salomon, M. F.; Pardo, S. N.; Salomon, R. G. J. Am. Chem. Soc. 1984,106, 3797. Pardo, S. N.; Ghosh, S.; Salomon, R. G. Tetrahedron Lett. 1981,22,1885. In the deoxygenation step of Scheme II of this reference, Li/NH3 should be used; in out hands the procedure reported in Table I of ref 5c did not work.
6. Vig, O. P.; Salota, J. P.; Sharma, M. P.; Sharma, S. D. Indian J. Chem. 1968, 6, 188.
7. Vig, O. P.; Vig, A. K.; Handa, V. K.; Sharma, S. D. Indian JChem. 1974, 12, 1158.
8. Cf. Kohler, H. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1980, 142.
9. Trost, B. M.; Arndt, H. C.; Strege, P. Verhoeven, T. R. Tetrahedron Lett. 1976, 39, 3477.
10. Cf. Fouchet, B.; Joucla, M.; Messager, J. C.; Toupet, L. J. Chem. Soc. Chem. Commun. 1982. 858.
11. Block, E. Reactions of Organosulfur Compounds; Academic: New York, 1978. Vacher, B.; Samat, A.; Chanon, M. Tetrahedron Lett. 1985, 26, 5129.
12. Ueno, Y.; Khare, R. K.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1983, 2637 and references therein.
13. Beckwith. A. L. J.: Schiesser. C. H. Tetrahedron 1985. 41. 3925.
14. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983,105, 3741. Begley, M. J.; Ladlow, M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1988, 1095.
15. Padwa, A.; Nimmsgern, H.; Wong, G. S. K. Tetrahedron Lett. 1985, 26. 957.
16. Beckwith, A. L. J.; Shea, D. M. Tetrahedron Lett. 1986, 27, 4525.
17. After submission of this manuscript further examples were published of radical closure onto the disubstituted terminus of a double bond: Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911.
18. Marvel, C. S.; Cowan, J. C. J. Am. Chem. Soc. 1939, 61, 3156.
19. Price, C. C.; Gillis, R. C. J. Am. Chem. Soc. 1953, 75, 4750.
20. Paquette, L. A.; Carr, R. V. C. Org. Synth. 1985, 64, 157.
21. Janousek, Z.; Piettre, S.; Gorissen-Hervens, F.; Viehe, H. G. J. Organomet. Chem. 1983. 250. 197.
22. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923. The compound should not be purified by distillation as it is thermally unstable.
23. Moffett, R. B. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 291.
24. Moffett, R. B.; Hart, C. A.; Hoehn, W. M. J. Am. Chem. Soc. 1947, 69, 1854.
25. Linstead, R. P.; Rydon, H. N. J. Chem. Soc. 1933, 580.