Reactions of polymer-supported α-selenoaldehydes with Grignard regents. A facile solid-phase stereoselective synthesis of (E)-1,2-disubstituted ethenes

Journal of the Chinese Chemical Society

Volumn 50, Issue 4, 2003, Pages 893-896

  Sheng, Shou Ri ^a,b   Huang, Xian ^a,c  

^a ZHEJIANG UNIVERSITY   (China)

^b JIANGXI NORMAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

(E) 1,2 Disubstituted ethene; Polymer supported (4 phenylseleno)morpholine; Polymer supported selenoaldehyde; Solid phase organic synthesis

Indexed keywords

EID: 33646236928     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200300125     Document Type: Article

References (44)

1. For recent reviews on SPOS, see: (a) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. 1996, 35, 17.
2. (b) Hermkens, P. H. H.; Ottenhijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
3. (c) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293.
4. (d) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549.
5. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091.
6. (f) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137.
7. Paulmier, C., Ed.; Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
8. (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697.
9. (b) Dumont, W.; Bayet, P.; Krief, A. Angew. Chem., Int. Ed. 1974, 13, 804.
10. (c) Seebac, D.; Beck, A. K. Angew. Chem., Int. Ed. 1974, 13, 805.
11. (d) Dumont, W.; Krief, A. Angew. Chem., Int. Ed. 1975, 14, 350.
12. (e) Van Ende, D.; Dumont, W.; Krief, A. Angew. Chem., Int. Ed. 1975, 14, 700.
13. (f) Van Ende, D.; Krief, A. Tetrahedron Lett. 1975, 16, 457.
14. (g) Lémion, A. M.; Krief, A. Tetrahedron Lett. 1976, 17, 3227.
15. (h) Sevrin, M.; Dumont, W.; Hevesi, L.; Krief, A. Tetrahedron Lett. 1976, 17, 2647.
16. (a) Lerouge, P.; Paulmier, C. Bull. Soc. Chim. Fr. 1985, 1219;
17. Related α-Selenenylating Aldehydes, see: (b) Reich, H. J.; Renga, J. M. J. Org. Chem. 1975, 40, 3313.
18. (c) Jefson, M.; Meinwald, J. Tetrahedron Lett. 1981, 22, 3561.
19. (a) Rémion, J.; Dumont, W.; Krief, A. Tetrahedron Lett. 1976, 17, 1385.
20. (b) Rémion, J.; Krief, A. Tetrahedron Lett. 1976, 17, 3743.
21. (c) Reich, H. J.; Chow, F. Chem. Commun. 1975, 790.
22. (a) Nicolaou, K. C.; Pastor, J.; Barluenga, S.; Winssinger, N. Chem. Commun. 1998, 1947.
23. (b) Ruhland, T.; Andersen, K.; Pedersen, H. J. Org. Chem. 1998, 63, 9204.
24. (c) Yanda, K.; Fujita, T.; Yanada, R. Synlett 1998, 971.
25. (d) Fujita, K.; Watanabe, K.; Oishi, A.; Ikeda, Y.; Taguchi, Y. Synlett 1999, 1760.
26. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q.; Kim, S.; Kessabi, J. Org. Lett. 1999, 1, 807.
27. (f) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734.
28. (g) Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew. Chem., Int. Ed. 2000, 39, 739.
29. (h) Nicolaou, K. C.; Winssinger, N.; Hughes, R.; Smethurst, C.; Cho, S. Y. Angew. Chem., Int. Ed. 2000, 39, 1084.
30. (i) Nicolaou, K. C.; Mitchell, H. J.; Fylaktakidou, K. C.; Suzuki, H.; Rodriguez, R. M. Angew. Chem., Int. Ed. 2000, 39, 1089.
31. (j) Nicolaou, K. C.; Roecker, A. J.; Pfefferkorn, J. A.; Cao, G.-Q. J. Am. Chem. Soc. 2000, 122, 2966.
32. (k) Fujita, K.; Taka, H.; Oishi, A.; Ikeda, Y.; Aguchi, Y.; Fujie, K.; Saeki, T.; Sakuma, M. Synlett 2000, 1509.
33. (l) Uehlin, L.; Wirth, T. Chimia 2001, 55, 65.
34. (m) Uehlin, L.; Wirth, T. Org. Lett. 2001, 3, 2931.
35. (a) Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828.
36. (b) Cram, D. J.; Greene, F. D. J. Am. Chem. Soc. 1953, 75, 6005.
37. Schmid, G. H.; Garratt, D. G. Tetrahedron Lett. 1975, 16, 3991.
38. Farrall, M. J.; Fréchet, J. M. J. J. Org. Chem. 1976, 41, 3877.
39. Zhu, L.-S.; Huang, X. Synth. Commun. 1997, 27, 39.
40. Wilmhurst, J. R. Aust. J. Chem. 1965, 8, 1759.
41. Vincent, S.; Armand, L. Bull. Soc. Chim. Fr. 1971, 3057.
42. Schlosser, M.; Müeller, G.; Christmann, K. F. Angew. Chem., Int. Ed. 1966, 5, 667.
43. Nakai, T.; Shiono, H.; Okawara, M. Chem. Lett. 1975, 249.
44. Klages, A. Ber. 1907, 40, 1768.