Aqueous Reactions with a Lewis Acid and an Organometallic Reagent. The Scandium Trifluoromethanesulfonate-Catalyzed Allylation Reaction of Carbonyl Compounds with Tetraallyltin

Journal of Organic Chemistry

Volumn 58, Issue 25, 1993, Pages 6958-6960

  Hachiya, Iwao ^a   Kobayashi, Shū ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751385645     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00077a009     Document Type: Article

References (30)

1. Reissig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71.
2. Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787.
3. For example: Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499 and references cited therein.
4. Schinzer, D., Ed. Selectivities in Lewis Acid Promoted Reactions; Kluwer Academic Publishers: Dordrecht, 1989.
5. Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds. Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982.
6. Kobayashi, S. Chem. Lett. 1991, 2087.
7. Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625.
8. Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1992, 33, 6815.
9. Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371.
10. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755.
11. The allylation reactions of carbonyl compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191.
12. Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910.
13. Petrier, C.; Einhorn, J.; Luche, J.-L. Tetrahedron Lett. 1985, 26, 1449.
14. Einhorn, C.; Luche, J.-L. J. Organomet. Chem. 1987, 322, 177.
15. Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697.
16. (O. Wilson, S. R.; Guazzaroni, M. E. J. Org. Chem. 1989, 54, 3087.
17. Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279.
18. Schmid, W.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 6674.
19. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
20. Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97.
21. For the reactions of carbonyl compounds with tetraalyltin, see: (a) Peet, W. G.; Tam, W. J. Chem. Soc, Chem. Commun. 1983, 853.
22. Daude, G.; Pereyre, M. J. Organomet. Chem. 1980, 190, 43.
23. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737.
24. See also: (d) Fukuzawa, S.; Sato, K.; Fujinami, T.; Sakai, S. J. Chem. Soc, Chem. Commun. 1990, 939. Quite recently, Yamamoto et al. reported allylation reactions of aldehydes with tetraallyltin in the presence of hydrochloric acid.
25. Inoue, H.; Yanagisawa, A.; Yamamoto, H. Abstracts of Papers, the 65th Annual Meeting of the Chemical Society of Japan, Tokyo, March 1993; 4G106, p 383.
26. (O Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc, in press.
27. Thom, K. F. US Patent 3615169 (1971);
28. Chem. Abstr. 1972, 76, 5436a.
29. Lewis acid-promoted allylation reactions of carbonyl compounds with allyltrialkyltin were reported. (a) Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 7107.
30. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 216.