Asymmetric addition of diethylzinc to benzaldehyde catalyzed by silica-immobilized titanium(IV) complexes of N-sulfonylated amino alcohols

Journal of Molecular Catalysis A: Chemical

Volumn 258, Issue 1-2, 2006, Pages 216-220

  Huang, Lu Ning ^a   Hui, Xin Ping ^a   Xu, Peng Fei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Asymmetric addition; Diethylzinc; N Sulfonylated amino alcohol; Silica immobilized catalyst; Titanium tetraisopropoxide

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; COMPLEXATION; SILICA; TITANIUM CARBIDE;

AMINO ALCOHOLS; ASYMMETRIC ADDITION; DIETHYLZINC; ENANTIOSELECTIVITY; TITANIUM TETRAISOPROPOXIDE;

ALCOHOLS;

EID: 33748455114     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.05.048     Document Type: Article

References (44)

1. For reviews, see:
2. Pu L., and Yu H.-B. Chem. Rev. 101 757 (2001)
3. Soai K., and Niwa S. Chem. Rev. 92 833 (1992)
4. Noyori R., and Kitamura M. Angew. Chem. Int. Ed. Engl. 30 (1991) 49
5. For reviews, see:
6. Fan Q.H., Li Y.M., and Chan A.S.C. Chem. Rev. 102 3385 (2002)
7. McNamara C.A., Dixon M.J., and Bradley M. Chem. Rev. 102 (2002) 3275
8. Clapham B., Reger T.S., and Janda K.D. Tetrahedron 57 (2001) 4637
9. Pu L. Chem. Eur. J. 5 (1999) 2227
10. Abramson S., Laspéras M., and Chiche B. J. Mol. Catal. A 165 (2001) 231
11. Bellocq N., Abramson S., Laspéras M., Brunel D., and Moreau P. Tetrahedron: Asymmetry 10 (1999) 3229
12. Laspéras M., Bellocq N., Brunel D., and Moreau P. Tetrahedron: Asymmetry 9 (1998) 3053
13. Soai K., Watanabe M., and Yamamoto A. J. Org. Chem. 55 (1990) 4832
14. Abramson S., Laspéras M., Galarneau A., Desplantier-Giscard D., and Brunel D. Chem. Commun. (2000) 1773
15. Fraile J.M., Mayoral J.A., Serrano J., Pericàs M.A., Solà L., and Castellnou D. Org. Lett. 5 (2003) 4333
16. Bae S.J., Kim S.W., Hyeon T., and Kim B.M. Chem. Commun. (2000) 31
17. Walsh P.J. Acc. Chem. Res. 36 (2003) 739
18. Duthaler R.O., and Hafner A. Chem. Rev. 92 (1992) 807
19. For recent examples, see:
20. Sellner H., and Seebach D. Angew. Chem. Int. Ed. Engl. 38 1918 (1999)
21. Cherng Y.-J., Fang J.-M., and Lu T.-J. J. Org. Chem. 64 (1999) 3207
22. Omote M., Kominato A., Sugawara M., Sato K., Ando A., and Kumadaki I. Tetrahedron Lett. 40 (1999) 5583
23. For recent examples, see:
24. Yang X.W., Sheng J.H., Da C.S., Wang H.S., Su W., Wang R., and Chan A.S.C. J. Org. Chem. 65 295 (2000)
25. Makamura Y., Takeuchi S., Ohgo Y., and Curran D.P. Tetrahedron Lett. 41 (2000) 57
26. Kostova K., Genov M., Philipova I., and Dimitrov V. Tetrahedron: Asymmetry 11 (2000) 3253
27. Huang W.S., and Pu L. J. Org. Chem. 64 (1999) 4222
28. For recent examples, see:
29. Balsells J., and Walsh P.J. J. Am. Chem. Soc. 122 3250 (2000)
30. Prieto O., Ramón D.J., and Yus M. Tetrahedron: Asymmetry 11 (2000) 1629
31. Paquette L.A., and Zhou R. J. Org. Chem. 64 (1999) 7929
32. Qiu J., Guo C., and Zhang X.-M. J. Org. Chem. 62 (1997) 2625
33. For recent examples, see:
34. Yus M., Ramón D.J., and Preito O. Tetrahedron: Asymmetry 13 1573 (2002)
35. Bauer T., Tarasiuk J., and Pasniczek K. Tetrahedron: Asymmetry 13 (2002) 77
36. Heckel A., and Seebach D. Angew. Chem. Int. Ed. Engl. 39 (2000) 163
37. Heckel A., and Seebach D. Chem. Eur. J. 8 (2002) 559
38. Noller C.R. Org. Syn. Coll. 2 (1951) 184
39. Reetz M.T., Drewes M.W., and Schmitz A. Angew. Chem. Int. Ed. Engl. 26 (1987) 1141
40. Bouh A.O., Rice G.L., and Scott S.L. J. Am. Chem. Soc. 121 (1999) 7201
41. Blitz J.P., Meverden C.C., and Diebel R.E. Langmuir 14 (1998) 1122
42. Hutter R., Dutoit D.C.M., Mallat T., Schneider M., and Baiker A. Chem. Commun. 26 (1995) 163
43. Maschmeyer T., Rey F., Sankar G., and Thomas J.M. Nature 378 (1995) 159
44. 4 was calculated by the amount of Ti(IV)