Desymmetrization of prochiral anhydrides with Evans' oxazolidinones: An efficient route to homochiral glutaric, and adipic acid derivatives

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1999, Pages 257-264

  Verma, Rekha ^a   Mithran, Seturam ^a   Ghosh, Sunil K ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001937498     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808838a     Document Type: Article

References (35)

1. Fora review: R. S. Ward, Clicm. Soc. Rev., 1990, 19, I.
2. (a) H. Imado, T. Ishizuka, and T. Kunieda, Tetrahedron Lett., 1995, 36, 931, and references cited therein;
3. (b) M. North, and G. Zagotto, Synlfii, 1995, 639;
4. I. G. Jones, W. Jones, M. North, M. Teijeira, and E. Uriate, Tetrahedron Lett., 1997,38,889;
5. G. Jaeschke, and D. Seebach, J. Org. Cliem., 1998, 63, 1190.
6. (a) K. Osakada, M. Obana, T. Ikariya, M. Saburi, and S. Yoshikawa, Tetrahedron Lett., 1981, 22, 4297;
7. (b) Y. Kawakami, J. Hiratake, Y. Yamamoto, and J. Oda, J. Client. Soc., Client. Commun., 1984, 779;
8. J. Hiratake, Y. Yamamoto, and J. Oda, J. Client. Soc., diem. Commun., 1985, 1717;
9. J. Hiratake, M. Inagaki, Y. Yamamoto, and J. Oda, J. Client. Sue., Perkin Trans. 1, 1987, 1053;
10. (e) Y. Nagaö, Y. Hagivvara, Y. Hascgawa, M. Ochiai, T. Inoue, M. Shiro, and E. Fujita, Client. Leu., 19S8, 381;
11. (f) D. S. Karanewsky, M. F. Malley, and J. Z. Goucoutas, J. Org . Client., 1991, 56, 3744;
12. (g) Y. Suda, S. Yago, M. Shiro, and T. Taguchi, Cliem. Lett., 1992, 389;
13. (h) K. Matsuki, H. Inoue, and M. Takcda, Tetrahedron Lett., 1993, 34,1167.
14. (a) T. Rosen, and C. H. Heathcock. J. Am. Client. Sue., 1985, 107, 3731;
15. (b) P. D. Theisen, and C. H. Heathcock, J. Org. Client., 1988, 53, 2374;
16. P. D. Theisen, and C. H. Heathcock, J. Org. Client., 1993,58,142.
17. R. Verma, and S. K. Ghosh, Cliem. Commun., 1997, 1601.
18. (a) D. A. Evans, and A. S. Kirn, in Encyclopedia of reagents 'for organic synthesis, ed. L. A. Paquette, Wiley, NY, 1995, vol. 11, p. 345;
19. (b) D. Ager, I. Prakash, and D. R. Schaad, Client. Rev., 1996, 96.835.
20. (a) E. Badder, W. Bartmann, G. Beck, A. Bergmann, H. W. Fehlhaber, H. Jendralla, K. Kesseler, R. Saric, H. Schussler, V. Teetz, M. Weber, and G. Wess, Tetrahedron Lett., 1988, 29, 2563;
21. (b) L. Novak, J. Rohaly, L. Poppe, G. Hornsyanszky, P. Kolonits, I. Zelei, I. Feher, J. Fekete, E. Szabo, U. Zaharszky, A. Javor, and C. Szantay, Liehigs Ann. Client., 1992, 145.
22. (a) I. Fleming, and S. K. Ghosh, J. Cliem. Soc., Clicm. Commun., 1992, 1775, and 1777; I. Fleming, and S. K. Ghosh, J. Cliem. Soc., Perkin Trans. 1, 1998, 2711;
23. (b) I. Fleming, and S. K. Ghosh, J. Clicm. Soc., Client. Commun., 1994, 2285, and 2287; I. Fleming, and S. K. Ghosh, J. Client. Soc., Perkin Traits. I, 1998,2733.
24. K. Takeshita, Y. Seki, K. Kawamoto, S. Murai, and N. Sonoda, J. Org. Client., 1987,52,4864.
25. A. P. Krapcho, Synthesis, 1982, 805.
26. I. Fleming, Stereocontrol in Organic Synthesis Using Silicon Compounds, Conferencias Plenarias de la XXIII Reunion Bienal de Quimica, Salamanca, 1990, 89.
27. H. L. Lochte, and P. L. Pickard, J. Am. Client. Soc., 1946,68, 721.
28. (a) I. Fleminc, in Organocopper Reagents: A Practical Approach, ed. R. J. K. Taylor, OUP, Oxford,' 1995, ch. 12, pp. 257-292;
29. (b) R. A. N. C. Crump, I. Fleming, J. H. M. Hill, D. Parker, N. L. Reddy, and D. Waterson, J. Cliem. Soc., Perkin Trans, l, 1992, 3277.
30. 1. Fleming, R. Henning, D. C. Parker, H. E. Plaut, and P. E. J. Sanderson.y. Client. Soc., Perkin Trans. I, 1995, 317.
31. D. A. Evans, T. C. Briton, J. A. Ellman, and R. L. Dorow, J. Am. Chem.Soc., 1990, 112,4011.
32. I. Fleming, and S. K. Ghosh, J. Cliem. Soc., Client. Commun., 1994, 99.
33. A. J. Irwin, and J. B. Jones, J. Am. Cliem. Soc., 1977,99, 556.
34. S. K. Ghosh, S. Chattopadhyay, and V. R. Mamdapur, Tetrahedron, 1991,47,3089.
35. D. A. Evans, and A. E. Weber, J. Am. Cliem. Sue., 1986,108, 6757.