Preparation and application of polymer-grafted Ti-BINOL complexes as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes

Tetrahedron

Volumn 56, Issue 22, 2000, Pages 3511-3516

  Yang, Xiaowu ^a   Su, Wu ^a   Liu, Daxue ^a   Wang, Hengshan ^a   Shen, Jianheng ^a   Da, Chaoshan ^a   Wang, Rui ^a   Chan, Albert S C ^b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Aldehydes; Enantioselective addition; Ti BINOL complexes

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; ALDEHYDE DERIVATIVE; DIETHYLZINC; TITANIUM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034717175     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00260-X     Document Type: Article

References (35)

1. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
2. (b) Merrifield, R. B. Science 1986, 232, 341.
3. (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
4. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527.
5. (c) Gravert, D.; Janda, K. Chem. Rev. 1997, 97, 489.
6. (d) Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
7. (a) Li, T.; Janda, K. D.; Ashley, J. A.; Lerner, R. A. Science 1994, 264, 1289.
8. (b) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sandera, J. K. M. J. Org. Chem. 1998, 63, 6309.
9. (c) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta. 1996, 79, 1710.
10. (d) Canali, L.; Cowan, E.; Deleuze, H.; Gibson, C. L.; Sherrington D. C. Chem. Commun. 1998, 2561.
11. (e) Altava, B.; Burguete, M. I.; Escuder, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126.
12. (f) Dreisbach, C.; Wischnewski, G.; Kragl, U.; Wandrey, C. J. Chem. Soc., Perkin. Trans. 1 1995, 875.
13. (a) Chan, A. S. C.; Huang, T. T.; Fan, Q. H.; Pai, C. C.; Li, Y. C. Huaxie 1997, 55, 117.
14. (b) Pu, L. Chem. Rev. 1998, 98, 2405.
15. (c) Kagan, H.; Riant, O. Chem. Rev. 1992, 92, 1007.
16. (d) Roshini, C.; Franzini, L.; Raffaelli, A.; Salladori, P. Synthesis 1992, 503.
17. Bayston D.J., Travers C.B., Polywka M.E.C. Tetrahedron: Asymmetry. 9:1998;20152018.
18. (a) Huang, W. S.; Hu, Q. S.; Zhang, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313.
19. (b) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1. 1998, 2131.
20. (c) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
21. (a) Kitajima, H.; Ito, K.; Katsuki, T. Chem. Lett. 1996, 343.
22. (b) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
23. (a) Zhang, F. Y.; Yip, C. W.; Cao, R.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 585.
24. (b) Zhang, F. Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651.
25. (c) Chan, A. S. C.; Zhang, F. Y.; Yip, C. W. J. Am. Chem. Soc. 1997, 119, 4080.
26. (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
27. (b) Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280.
28. (c) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
29. Halm C., Kurth M. Angew. Chem., Int. Ed. Engl. 37:1998;510.
30. (a) Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002.
31. (b) Yang, D.; Yip, Y. C.; Chen, J.; Cheung, K. K. J. Am. Chem. Soc. 1998, 120, 7659.
32. (c) Corey, E. J.; Helal, C. J. Tetrahedron: Lett. 1995, 36, 9153.
33. (a) Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem. 1988, 27, 566.
34. (b) Chan, A. S. C.; Hu, W.; Pai, C. C.; Lau, C. P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570.
35. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 3133.