A simple synthetic method for chiral 1,2-epoxides and the total synthesis of a chiral pheromone epoxide

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 1, 2000, Pages 53-57

  Zhang, Zhi Bo ^a   Wang, Zhi Min ^a   Wang, Yu Xiu ^a   Liu, Huan Quan ^a   Lei, Gui Xin ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; LITHIUM COMPOUNDS; PURIFICATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

OPTICAL PURITY;

ESTERS;

EID: 0034614727     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907396e     Document Type: Article

References (25)

1. T. Liljetors, M. Bengtsson and B. S. Hansson, J. Chem. Ecol., 1987, 13, 2023;
2. E. Hecker and A. Butenanot, in Techniques in Pheromone Research, ed. H. E. Hummel and T. A. Miller, Springer-Verlag, New York, 1984, eh. 1, pp. 1-44;
3. W. L. Roelofs, in Chemical Ecology: Odour Communication in Animals, ed. F. J. Ritter, Elsevier/North Holland Biomedical Press, New York, 1979, pp. 159-168;
4. W. L. Roelofs, A. Hill and R. Carde, J. Chem. Ecol, 1975, 1, 83;
5. J. A. Klun, O. L. Chapman, K. C. Mattes, P. W. Wojtkowski, M. Beroza and P. E. Sonnet, Science, 1973, 181, 661.
6. K. Mori, in Techniques in Pheromone Research, ed. H. E. Hummel and T. A. Miller, Springer-Verlag: New York, 1984, eh. 12, pp. 323-370;
7. T. W. Bell and J. Meinwald, J. Chem. Ecol., 1986, 12, 383;
8. J. Wunderer, K. Hansen, T. W. Bell, D. Schneider and J. Meinwald, J. Exp. Biol., 1986, 46, 11;
9. K. Hansen, Physiol. Entomol., 1984, 9, 9;
10. D. Schneider, in Comparative Physiology of Sensory Systems, ed. L. Bolis, R. D. Keynes and S. H. P. Maddrell, Cambridge University Press, London, 1984, p. 301.
11. K. Mori, Chirality, 1998, 10, 578.
12. J. W. Wong, E. W. Underhill, S. L. McKenzie and M. D. Chisholm, J. Chem. Ecol., 1985, 11, 726 and references cited therein.
13. J. S. Yadav and P. Radhakrishna, Tetrahedron, 1990, 46, 5825 and references cited therein.
14. G. B. Payne, J. Org. Chem., 1962, 27, 3819.
15. T. W. Bell and J. A. Clacclo, Tetrahedron Lett., 1988, 29, 865 and references cited therein.
16. J. S. Yadav, M. Y Valli and A. R. Prasad, Tetrahedron, 1998, 54, 7551 and references cited therein.
17. T. Soulie, T. Boyer and J. Y. Lallemand, Tetrahedron: Asymmetry, 1995, 6, 625.
18. H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483.
19. Z.-B. Zhang, Z.-M. Wang, Y.-X. Wang, H.-Q. Liu, G.-X. Lei and M. Shi, Tetrahedron: Asymmetry, 1999, 10, 837.
20. G.-Q. Lin, Z.-X. Tan and Y.-W. Wu, Acta Chim. Sin., 1984, 42, 1178.
21. The ee was determined by Chiral HPLC (Chiralcel OD).
22. C. Eisenberg and P. Knochel, J. Org. Chem., 1994, 59, 3746.
23. T. Ebata and K. Mori, Agric. Biol. Chem., 1989, 53, 801;
24. T. W. Bell and J. Ciaccio, J. Org. Chem., 1993, 58, 5153.
25. K. Mori and T. Ebata, Tetrahedron, 1986, 42, 3471.