Highly efficient synthesis of homoallylic alcohols and amines via allylation of aldehydes and imines catalyzed by ZrOCl2·8H2O in water

Tetrahedron Letters

Volumn 49, Issue 25, 2008, Pages 4047-4049

  Shen, Wei ^a   Wang, Li Min ^a   Feng, Jian Jun ^a   Tian, He ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Allylation; Allyltin; Water as solvent; ZrOCl2 8H2O

Indexed keywords

ALLYL ALCOHOL; ALLYL COMPOUND; ALLYLTRIBUTYLSTANNANE; AMINE; BENZALDEHYDE; IMINE; INORGANIC SALT; LEWIS ACID; WATER; ZIRCONYL CHLORIDE;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 43449120142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.084     Document Type: Article

References (37)

1. Yanagisawa A., Nakashima H., Ishiba A., and Yamamoto H. J. Am. Chem. Soc. 118 (1996) 4723
2. Loh T.P., Xu J., Hu Q.Y., and Vittal J.J. Tetrahedron: Asymmetry 11 (2000) 1565
3. Loh T.P., and Xu J. Tetrahedron Lett. 40 (1999) 2431
4. Loh T.P., and Zhou J.R. Tetrahedron Lett. 41 (2000) 5261
5. Hamasaki S., Chounan Y., Horino H., and Yamamoto Y. Tetrahedron Lett. 41 (2000) 9883
6. Nagayama S., and Kobayashi S. Angew. Chem., Int. Ed. 93 (2000) 567
7. Shibata I., Yoshimura N., Yabu M., and Baba A. Eur. J. Org. Chem. (2001) 3207
8. Kobayashi S., Aoyama N., and Manabe K. Synlett (2002) 483
9. Aspinall H.C., Bissett J.S., Greeves N., and Levin D. Tetrahedron Lett. 43 (2002) 319
10. Andrade C.K.Z., Azevedo N.R., and Oliveira G.R. Synthesis (2002) 928
11. Kobayashi S., Aoyama N., and Manabe K. Chirality 15 (2003) 124
12. Vartoli G., Bosco M., Giuliani A., Marcantoni E., Palmieri A., Petrini N., and Sambri L. J. Org. Chem. 69 (2004) 1290
13. Nishiyama Y., Kakushou F., and Sonoda N. Tetrahedron Lett. 46 (2005) 787
14. Das B., Laxminarayana K., Ravikanth B., and Ramarao B. Tetrahedron Lett. 47 (2006) 9103
15. Kalita H.R., Borah A.J., and PhuKan P. Tetrahedron Lett. 48 (2007) 5047
16. Akiyama T., Iwai J., Onuma Y., and Kagoshima H. Chem. Commun. (1999) 2191
17. Aspinall H.C., Bissett J.S., Greeves N., and Levin D. Tetrahedron Lett. 43 (2002) 323
18. Akiyama T., and Onuma Y. J. Chem. Soc., Perkin Trans. 1 (2002) 1157
19. Yadav J.S., Reddy B.V.S., Raju A.K., and Gnaneshwar D. Adv. Synth. Catal. 344 (2002) 938
20. Yadav J.S., Reddy B.V.S., and Raju A.K. Synthesis (2003) 883
21. Yin Y.Y., Zhao G., and Li G.L. Tetrahedron 61 (2005) 12042
22. Das B., Ravikanth B., Laxminarayana K., and Rao B.V. J. Mol. Catal. A: Chem. 253 (2006) 92
23. Li G.L., and Zhao G. Org. Lett. 8 (2006) 633
24. Das B., RaviKanth B., Thirupathi P., and Rao B.V. Tetrahedron Lett. 47 (2006) 5041
25. Hoenberer K.R., Hamblet C.L., and Leighton J.L. J. Am. Chem. Soc. 122 (2000) 12894
26. Nicolaou K.C., Khim D.W., and Baati R. Angew. Chem., Int. Ed. 41 (2002) 3701
27. Enders R.D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895
28. Bloch R. Chem. Rev. 98 (1998) 1407
29. For reviews, see:. Li C.J. Chem. Rev. 93 (1993) 2023
30. Li C.J., and Chan T.H. Organic Reactions in Aqueous Media (1997), John Wiley, New York
31. Grieco P.E. Organic Reactions in Water (1998), Blackie Academic & Professional, London
32. Lindstrom U.M. Chem. Rev. 102 (2002) 2751
33. Li C.J. Chem. Rev. 105 (2005) 3095
34. Herrerias C.I., Yao X.Q., Li Z.P., and Li C.J. Chem. Rev. 107 (2007) 2546
35. Eftekhari S.B., Abdollahifar A., Hashemi M.M., and Zirak M. Eur. J. Org. Chem. (2006) 5152
36. Reddy C.S., and Nagaraj A. Heterocycl. Commun. 13 (2007) 67
37. Shen W., Wang L.M., and Tian H. J. Fluorine Chem. 129 (2008) 267