Allylindation of 6-substituted 2-hydroxy-l-tetralones in aqueous and organic media. stereochemistry and competition studies

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6990-6998

  Lobben, Paul C ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000926764     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980825f     Document Type: Article

References (32)

1. Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.. Williamson, T., Eds.; Oxford University Press: Oxford, 1998; pp 250-264.
2. Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996,118,1931.
3. Paquette, L. A.; Lobben, P. C. J. Org. Chem. 1998, 63, 5604.
4. (a) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130.
5. (b) Frye, S. V.; Eliel, E. L.; Cloux, R. J. Am. Chem. Soc. 1987, 109, 1862.
6. Lambert, J. B. In The Conformational Analysis of Cyclohexenes, Cydohexadienes, and Related Hydroaromatic Compounds; Rabideau, P., Ed.; VCH: New York, 1989; pp 47-63.
7. Fraser, R. R.; Faibish, N. C. Can. J. Chem. 1995, 73, 88 and relevant references therein.
8. Johnson, F. Chem. Rev. 1968, 68, 375.
9. Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1978, 43, 1599.
10. Giardina, G.; Clarke, G. D.; Dondio, G.; Pétrone, G.; Sbacchi, M.; Vecchietti, V. J. Med. Chem. 1994, 37, 3482.
11. (a) Moriarty, R. M.; Engerer, S. C.; Prakash, O.; Prakash, I.; Gill, U. S.; Freeman, W. A. J. Org. Chem. 1987,52,153 and references therein
12. (b) Irie, H.; Matsumoto, R.; Nishimura, M.; Zhang, Y. Chem. Pharm. Bull. 1990, 38, 1852.
13. Stork, G. J. Am. Chem. Soc. 1947, 69, 576.
14. Allinger, N. L.; Jones, E. S. J. Org. Chem. 1962, 27, 70.
15. Sharpless, K. B.; Lauer, R. F. J.Am. Chem. Soc. 1973,95,7917;
16. Sharpless, K. B.; Lauer, R. F. J.Am. Chem. Soc. 1972,94,7154.
17. Toromanoff, E. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Interscience: New York, 1967; Vol. 2, p 157.
18. (a) Hennion, G. F.; O'Shea, F. X. J. Am. Chem. Soc. 1958, 80, 614.
19. (b) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 738.
20. Kienzle, F.; Mayer, M. Helv. Chim. Acta 1978,61,2609.
21. Caine, D.; Smith, T. L., Jr. J. Am. Chem. Soc. 1980,102, 7568.
22. (e) Findlay, J. A.; Dcsai, D. N.; Lonergan, G. C.; White, P. S. Can. J. Chem. 1980, 58, 2827.
23. (f) Kuwajima, I.; Nakamura, E.; Hashimoto, K. Tetrahedron 1983,39, 975.
24. (g) Stork, G.; Stryker, J. M. Tetrahedron Lett. 1983,24, 4887.
25. (h) Fleming, I.; Terreth, N. K. J. Organomet. Chem. 1984, 264, 99.
26. Trost, B. M.; Florez, J.; Jebaratnam, D. J. J. Am. Chem. Soc. 1987,109, 613.
27. (j) Idrissi, M. E.; Santelli, M. J. Org. Chem. 1988, 53, 1010.
28. (k) Trost, B. M.; Florez, J.; Haller, K. J. J. Org. Chem. 1988,53, 2394.
29. (a) Wu, Y.-D.; Houk, K. N.; Trost, B. M. J. Am. Chem. Soc. 1987, 709, 5560.
30. (b) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991,56, 3656.
31. Vcdejs, E.; Dent, W. H., Ill; Kendall, J. T.; Oliver, P. A. J. Am. Chem. Soc. 1996, 118, 3556.
32. For generic experimental details, see: Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917.