Enantiotopic-group differentiation. Catalytic asymmetric ring-opening of prochiral cyclic acid anhydrides with methanol, using cinchona alkaloids

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1987, Pages 1053-1058

  Hiratake, Jun ^a   Inagaki, Minoru ^a   Yamamoto, Yukio ^a   Oda, Jun'ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049072812     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19870001053     Document Type: Article

References (32)

1. S. Terashima and S. Yamada, Tetrahedron Lett., 1977, 1001
2. Y. Nagao, T. Inoue, and E. Fuljita, Tetrahedron, 1984, 40, 1215.
3. I. J. Jokovac, H. B. Goodbrand, K. P. Lok, and J. B. Jones, J. Am. Chem. Soc, 1982, 104, 4659.
4. Ching-Shih Chen, Y. Fujimoto, and C. J. Sih, J. Am. Chem. Soc, 1981,103, 3580
5. C. J. Francis and J. B. Jones, J. Chem. Soc, Chem. Commun., 1984, 579.
6. Y. Kawakami, J. Hiratake, Y. Yamamoto, and J. Oda, J. Chem. Soc, Chem. Commun., 1984, 779
7. Y. Kawakami, J. Hiratake, Y. Yamamoto, and J. Oda Agric Biol. Chem., 1986, 50, 693.
8. H. Hiemstra and H. Wynberg, J. Am. Chem. Soc, 1981, 103, 417.
9. U. Eder, G. Sauer, and R. Wiechert, Angew. Chem., Int. Ed. Engl., 1971, 10,496
10. Z. G. Hajos and D. R. Parrish, J. Org. Chem., 1974, 39, 1615.
11. For a preliminary report J. Hiratake, Y. Yamamoto, and J. Oda, J. Chem. Soc, Chem. Commun., 1985, 1717.
12. P. F. Wiley, K. Gerzon, E. H. Flynn, M. V. Sigal Jr., O. Weaver, U. C. Quarck, R. R. Chauvette, and R. Monahan, J. Am. Chem. Soc, 1957, 79, 6062.
13. J. N. Edmund and J. F. Thorpe, J. Chem. Soc, Trans., 1920,117,1465.
14. G. Yabuta and K. Mori, Nippon Nogei Kagaku Kaishi, 1982,56,1121 (Chem. Abstr., 1983, 98, 179156d).
15. P. Lewerand, J. MacMillan, J.Chem.Soc.,Perkins Trans. 1, 1983,1417.
16. M. J. Devos, J. N. Denis, and A. Krief, Tetrahedron Lett., 1978, 1847.
17. J. Suszko and F. Szelag, Bull. Int. Acad. Pol. Sci. Lett., Cl. Sci. Math. Nat., Ser. A, 1936, 403.
18. V. Prelog and M. Wilhelm, Helv. Chim. Acta, 1954, 37, 1634.
19. N. Kobayashi and K. Iwai, J. Org. Chem., 1981, 46, 1823
20. N. Kobayashi, Br. Polym. J., 1984, 16, 205.
21. K. Hermann and H. Wynberg, J. Org. Chem., 1979, 44, 2238.
22. J. W. Cornforth, R. H. Cornforth, G. Popjak, and L. Yengoyan, J. Biol. Chem., 1966, 241, 3970.
23. C. F. Lane, H. L. Myatt, J. Daniels, and H. B. Hopps, J. Org. Chem., 1974, 39, 3052.
24. R. J. E. Talbot, in ‘Comprehensive Chemical Kinetics,’ eds. C. H. Bamford and C. F. H. Tipper, Elsevier, Amsterdam, 1972, vol. 10, p. 286.
25. J. Murto, in ‘The Chemistry of the Hydroxyl Group,’ ed. S. Patai, Interscience, London, 1971, p. 1106.
26. W. E. Doering, G. Cortes, and L. H. Knox, J. Am. Chem. Soc, 1947, 69, 1700.
27. C. F. Lane, Synthesis, 1975, 135.
28. P. Rabe, Justus Liebigs Ann. Chem., 1932, 492, 242.
29. A. J. Irwin and J. B. Jones, J. Am. Chem. Soc, 1977, 99, 556.
30. R. H. Cornforth, J. W. Cornforth, and G. Popjak, Tetrahedron, 1962, 18, 1351.
31. W. K. Wilson, T. J. Scallen, and C. J. Morrow, J. Lipid Res., 1982, 23, 645.
32. T. Mukaiyama, H. Yamashita, and M. Asami, Chem. Lett., 1983.