Diastereoselective epoxidation of camphor N-enoylpyrazolidinones

Journal of the Chinese Chemical Society

Volumn 50, Issue 5, 2003, Pages 1047-1051

  Fan, Chai Ling ^a   Reddy, Gondi Sudershan ^a   Chen, Kwunmin ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

Asymmetric; Camphor; Chiral auxiliary; Diastereoselectivity; Epoxide; Lewis acid; Mechanism; Stereoinduction

Indexed keywords

EID: 0344538759     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200300148     Document Type: Article

References (27)

1. (a) Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543.
2. (b) Amano, S.; Ogawa, N.; Ohtsuka, M.; Chida, N. Tetrahedron 1999, 55, 2205.
3. (a) Sharpless, K. B. Aldrichim. Acta 1983, 16, 67.
4. (b) Behrens, C. H.; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189.
5. (c) Jorgensen, K. A. Chem. Rev. 1989, 89, 431.
6. (a) Page, P. C. B.; Rassias, G. A.; Barros, D.; Ardakani, A.; Buckley, B.; Bethell, D.; Smith, T. A. D.; Slawin, M. Z. J. Org. Chem. 2001, 66, 6926.
7. (b) Daly, A. M.; Renehan, M. F.; Gilheany, D. G. Org. Lett. 2001, 3, 663.
8. (c) Hoshino, Y.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10452.
9. (d) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis Ed.: Ojima, I. VCH, New York. 1993, 103.
10. (e) Jacobsen, E. N.; Zhang, W.; Muci, A. M.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
11. (a) Yang, D.; Jiao, G.-S.; Yip, Y.-C.; Wong, M.-K. J. Org. Chem. 1999, 64, 1635. and refs therein.
12. (b) Adam, W.; Pastor, A.; Peters, K.; Peters, E.-M. Org. Lett. 2000, 2, 1019.
13. (c) Adam, W.; Schambony, S. B. Org. Lett. 2001, 3, 79.
14. Adam, W.; Hadjiarapoglou, L. In Topics of Current Chemistry; Herrmann, W. A.; Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; Vol. 164, p 45.
15. (a) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E. Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M. Wu, L. E. Chem. Commun., 1997, 739.
16. (b) Cooper, M. S. Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, 533.
17. (a) Yang, K. S.; Lain, J. C.; Lin, C. H.; Chen, K. Tetrahedron Lett. 2000, 41, 1453.
18. (b) Lin, C. M.; Yang, K. S.; Pan, J. F.; Chen, K. Tetrahedron Lett. 2000, 41, 6815.
19. (c) Yang, K. S.; Chen, K. Org. Lett. 2000, 2, 729.
20. (d) Yang, K. S.; Chen, K. J. Org. Chem. 2001, 66, 1676.
21. (a) Murase, N.; Hoshino, Y.; Oishi, M.; Yamamoto, H. J. Org. Chem. 1999, 64, 338.
22. (b) Yoon, H.; Burrows, C. J. J. Am. Chem. Soc. 1988, 110, 4087.
23. (c) Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345.
24. (d) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
25. Adam, W.; Smerz, A. Bull. Soc. Chem. Belg. 1996, 105, 581.
26. Rebek, J., Jr.; Marshall, L.; McManis, J.; Wolak, R. J. Org. Chem. 1986, 51, 1649.
27. 7b,7d