(Salen)Ti(IV)-catalyzed asymmetric ring-opening of monosubstituted epoxides with dithiophosphorus acid

Letters in Organic Chemistry

Volumn 2, Issue 8, 2005, Pages 752-754

  Zhou, Zhenghong ^a   Wang, Quanyong ^a   Liu, Bing ^a   Zhao, Guofeng ^a   Zhou, Qilin ^a   Tang, Chuchi ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

(Salen)Ti(IV) complex; Asymmetric ring opening; Enantioselectivity; Monosubstituted epoxides; Regioselectivity

Indexed keywords

EID: 33751320013     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017805774717436     Document Type: Review

References (37)

1. (a) Pastor, I. M.; Yus, M. Current Org. Chem. 2005, 9, 1;
2. (b) Hodgson, D. M.; Gibbs, A. R.; Lee, G. D. Tetrahedron 1996, 52, 14361;
3. (c) Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1197.
4. (a) Fan, R. H.; Hou, X. L. J. Org. Chem. 2003, 68, 726;
5. (b) Yadav, J. S.; Reddy, B. V. S.; Baishya, G. Chem. Lett. 2002, (9), 906;
6. (c) Younes, M. R.; Chaabouni, M. M.; Baklouti, A. Tetrahedron Lett. 2001,42, 3167;
7. (d) Kwsavan, V.; Delpon, D. B.; Begue, J. P. Tetrahedron Lett. 2000,41, 2895;
8. (e) Adams, H.; Bell, R.; Cheung, Y. Y. Tetrahedron: Asymmetry 1999, 10, 4129;
9. (f) Wu, J.; Hou, X. L.; Dai, L. X.; Xia, L. J.; Tang, M. H. Tetrahedron: Asymmetry 1998,9, 3431;
10. (g) Wu, M. A.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252;
11. h) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783;
12. (i) Fukuzawa, S.-I.; Kato H.; Ohtaguchi, M.; Hayashi, Y.; Yamazaki, H. J. Chem. Soc., Perkin Trans. 1 1997, 3059;
13. (j) Albanese, D.; Landin, D.; Penso, M. Synthesis 1994, 34;
14. (k) Maiti, A. K.; Bhattacharyya, P. Tetrahedron 1994,50, 10483;
15. (l) Yamashita, H. Bull. Chem. Soc. Jpn. 1988,61, 1213;
16. m) Soo, Y. K.; Sharpless, K. B. J. Org. Chem. 1986, 51, 5413;
17. (n) Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985,50, 1560;
18. (o) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985,50, 1557.
19. (a) Pomar, J. C. J.; Soderquist, J. A. Tetrahedron Lett. 1998, 39, 4409;
20. (b) Tanabe, Y.; Mori, M.; Yoshida, Y. J. Chem. Soc., Perkin Trans. 1 1997, 671;
21. (c) Brittain, J.; Gareau, Y. Tetrahedron Lett. 1993,34, 3363.
22. (a) Li, Z. M.; Zhou, Z. H.; Li, K. Y.; Wang, L. X.; Zhou, Q. L.; Tang, C. C. Tetrahedron Lett. 2002, 43, 7609;
23. (b) Tamura, Y.; Kawasaki, T.; Yasuda, H. J. Chem. Soc. Perkin Trans. 1 1981, 1577;
24. (c) Pudovik, A. N.; Faezurrin, E. M.; Zhuravrev, G. E. Zh. Obshch. Khim. 1965, 36, 718;
25. (d) Mebah, J. M.; Ndong; Mieloszynski, J. L.; Paquer, D. Phosphorus Sulfur and Silicon 1993,78, 215;
26. (e) Aldasheva, A.; Beishekeev, Zh.; Dzhundubaev, K. D.; Toktobekova, T. Izv. Akad. Nauk. Kirg. SSR 1980, 4, 52 (Chem. Abstr. 1981,94, 12134).
27. Jacobsen, E. N. Acc. Chem. Res. 2000,33, 421.
28. Bruns, S.; Haufe, G. Tetrahedron: Asymmetry 1999,10, 1563.
29. (a) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2005,7, 1983;
30. (b) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Massaccesi, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 6, 2173;
31. (c) Bartoli, G.; Bosco, M.; Carlone, A; Locatelli, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004,6, 3973.
32. (a) Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 1939;
33. (b) Liang, S.; Bu, X. R. J. O. Chem. 2002,67, 2702.
34. (a) Zhou, X. G.; Huang, J. S.; Ko, P. H.; Cheung, K. K.; Che, C. M. J. Chem. Soc., Dalton Trans 1999, 3303;
35. (b) Bernardo, K. D. S.; Robert, A.; Dahan, F.; Meunier, B. New J. Chem. 1995, 19, 129;
36. (c) Takenaka, N.; Yong, H.; Rawal, V. H. Tetrahedron 2002, 58, 8299.
37. 31P NMR, and then purified by column chromatography on silica gel (200-300 mesh, gradient eluted with petroleum ether/ethyl acetate) to provide the ring-opening product 4 and 5. The ee value of the product was fdetermined by chiral HPLC analysis.