Gadolinium(III) chloride: a novel and an efficient reagent for the synthesis of homoallylic alcohols

Tetrahedron Letters

Volumn 47, Issue 26, 2006, Pages 4315-4318

  Lingaiah, B Venkat ^a   Ezikiel, G ^a   Yakaiah, T ^a   Reddy, G Venkat ^a   Rao, P Shanthan ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Allylation; Allylstannanes; Carbonyl compounds; Gadolinium chloride; Homoallylic alcohols

Indexed keywords

ACETONITRILE; ALCOHOL; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALLYL COMPOUND; CARBONYL DERIVATIVE; GADOLINIUM CHLORIDE; KETONE DERIVATIVE; REAGENT;

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

EID: 33646768210     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.124     Document Type: Article

References (43)

1. Denmark S.E., and Fu J.-P. Chem. Rev. 103 (2003) 2763
2. For examples see:. Keck G.E., Tarbet K.H., and Geraci L.S. J. Am. Chem. Soc. 115 (1993) 8467
3. Cosata A.L., Piazza M.G., Tagliavivi E., Trombini C., and Ronchi A.U. J. Am. Chem. Soc. 115 (1993) 7001
4. Yanagisawa A., Nakashima H., Ishiba A., and Yamamoto H. J. Am. Chem. Soc. 118 (1996) 4723
5. Yanagisawa A., Ishiba A., Nakashima H., and Yamamoto H. Synlett 88 (1996)
6. Yanagisawa A., Nakashima H., Nakatsuka Y., Ishiba A., and Yamamoto H. Bull. Chem. Soc. Jpn. 74 (2001) 1129
7. Hanawa H., Hashimoto H., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 1708
8. Cozzi P.G., Orioli P., Tagliavini E., and Umani-Ronchi A. Tetrahedron Lett. 38 (1997) 145
9. Loh T.-P. In: Yamamoto H. (Ed). Science of Synthesis (2004), Georg Thieme Velag Stuttgart, New York 413
10. Nicolaou K.C., Khim D.W., and Baati R. Angew. Chem., Int. Ed. 41 (2002) 3701
11. Hoenberer K.R., Hamblet C.L., and Leighton J.L. J. Am. Chem. Soc. 122 (2000) 12894
12. Felphin F.X., and Lebreton J. J. Org. Chem. 67 (2002) 9192
13. Yamamoto Y. Acc. Chem. Res. 20 (1987) 243
14. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207
15. Marshall J.A. Chem. Rev. 96 (1996) 31
16. Hachiya I., and Kobayashi S. J. Org. Chem. 58 (1993) 6958
17. Hamasaki S., Chounan Y., Horino H., and Yamamoto Y. Tetrahedron Lett. 41 (2000) 9883
18. Ley S.V., and Cox L.R. J. Chem. Soc., Perkin Trans. 1 (1997) 3315
19. Shibata I., Fukuoka S., Yoshimura N., Matsuda H., and Baba A. J. Org. Chem. 62 (1997) 3790
20. Roush W.S., Walts A.E., and Hoong L.K. J. Am. Chem. Soc. 107 (1985) 8186
21. Nagayama S., and Kobayashi S. Angew. Chem. Int. Ed. 93 (2000) 567
22. Kobayashi S., Aoyama N., and Manabe K. Synlett (2002) 483
23. Aspinall H.C., Bissett J.S., Greeves N., and Levin D. Tetrahedron Lett. 43 (2002) 319
24. Inoue K., Yasuda M., and Baba A. Synlett (1997) 699
25. Naruta Y., Ushida S., and Maruyama K. Chem. Lett. (1979) 919
26. Andrade C.K.Z., Azevedo N.R., and Oliveira G.R. Synthesis (2002) 928
27. Choudary B.M., Sreedhar Ch., and Shekar Ch.V.R. Synlett (2002) 1694-1696
28. Andrade C.K.Z., and Azevedo R. Tetrahedron Lett. 42 (2001) 6473
29. Davis A.P., and Jaspars M. J. Chem. Soc., Pekin Trans. 1 (1992) 2111
30. Takuwa A., Nishigaichi Y., Yamashitha K., and Iwamoto H. Chem. Lett. (1990) 1761
31. Roush W.R., Hoong L.K., Palmer M.A.J., and Park J.C. J. Org. Chem. 55 (1990) 4109
32. Fleming I., Donogues J., and Smithers R. Org. React. 37 (1989) 57
33. Hunter R., and Tomlinson G.D. Tetrahedron Lett. 30 (1989) 2013
34. Hosomi A., Endo M., and Sakurai H. Chem. Lett. 941 (1976)
35. McCluskey A., Mayer D.M., and Young D.J. Tetrahedron Lett. 38 (1997) 5217
36. Tanaka H., Yamashita S., Ikemoto Y., and Torii S. Tetrahedron Lett. 29 (1988) 1721
37. Komastu N., Uda M., Suzuki H., Takahashi T., Domae T., and Wada M. Tetrahedron Lett. 38 (1997) 7215
38. Ma Y., Qian C., Xie M., and Sun J. J. Org. Chem. 64 (1999) 6462
39. Lingaiah B.P.V., Reddy G.V., Yakaiah T., Narsaiah B., Reddy S.N., Yadla R., and Rao P.S. Synth. Commun. 34 (2004) 4431-4437
40. Reddy G.V., Maitraie D., Narsaiah B., Rambabu Y., and Rao P.S. Synth. Commun. 31 (2001) 2881
41. Aggarwal V.K., and Vennall G.P. Synthesis (1998) 1822
42. Cokley T.M., Harvey P.J., Marshall R.L., Mc Cluskey A., and Young D.J. J. Org. Chem. 62 (1997) 1961-1964
43. 4 and concentrated in vacuo, and the resulting product was purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate-hexane, 2:8) to afford pure homoallylic alcohol.