Stereospecific Methylation of γ,δ-Epoxy Acrylates by Trimethylaluminum: A Method for the Iterative The Construction of Polypropionate Chains

Journal of Organic Chemistry

Volumn 56, Issue 23, 1991, Pages 6483-6485

  Miyashita, Masaaki ^a   Hoshino, Masahide ^b   Yoshikoshi, Akira ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001726621     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00023a001     Document Type: Article

References (33)

1. Hoffmann, R. W.; Zeiss, H.-J. Angew. Chem., Int. Ed. Engl. 1980, 19, 218.
2. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873.
3. Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561.
4. Roush, W. R.; Haltermann, R. L. J. Am. Chem. Soc. 1986, 108, 294.
5. Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. J. Org. Chem. 1987, 52, 316.
6. Suzuki, K.; Tomooka, K.; Katayama, E.; Matsumoto, T.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 5221.
7. Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195.
8. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570.
9. Hanessian, S.; Murry, P. J. Can. J. Chem. 1986, 64, 2231.
10. Ziegler, F. E.; Kneisley, A. Heterocycles 1987, 25, 105.
11. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564.
12. Ziegler, F. E.; Kneisley, A.; Thottathil, J. K.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5534, 5442.
13. Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1986, 108, 6090.
14. Lipshutz, B. H.; Barton, J. C. J. Org. Chem. 1988, 53, 4495.
15. Pfaltz, A.; Mattenberger, A. Angew. Chem. Supplement 1982, 161.
16. Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597.
17. Roush, W. R.; Adam, M. A.; Peseckis, S. M. Tetrahedron Lett. 1983, 24, 1377.
18. Ibuka, T.; Tanaka, M.; Nemoto, H.; Yamamoto, Y. Tetrahedron 1989, 45, 435.
19. Nicolaou, K. C.; Uenishi, J. J. Chem. Soc., Chem. Commun. 1982, 1292.
20. Honda, Y.; Hirai, S.; Tsuchihashi, G. Chem. Lett. 1989, 255.
21. Storr, A.; Jones, K.; Laubengayer, A. W. J. Am. Chem. Soc. 1968, 90, 3173.
22. Harney, D. W.; Meisters, A.; Mole, T. Aust. J. Chem. 1974, 27, 1639.
23. Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
24. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
25. Heathcock, C. H. Comprehensive Carbanion Chemistry, Buncel, E., Dust, T., Eds.; Elsevier: Amsterdam, 1984; Vol. 2.
26. Heathcock, C. H. In Asymmetric Syntheses; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3.
27. Mukaiyama, T. Org. React. 1982, 28, 203.
28. Masamune, S.; Choy, W.; Peterson, J. S.; Sila, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
29. Masamune, S. Pure Appl. Chem. 1988, 60, 1587.
30. Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441.
31. Paterson, I.; Goodman, J. M. Tetrahedron Lett. 1989, 30, 997.
32. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976.
33. Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290.