Application of ferrocenyl substituted aziridinylmethanols (FAM) as chiral ligands in enantioselective conjugate addition of diethylzinc to enones

Tetrahedron Asymmetry

Volumn 18, Issue 5, 2007, Pages 679-684

  Isleyen, Alper ^a   Dogan, Özdemir ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; DIETHYLZINC; FERROCENE DERIVATIVE; LIGAND; METHANOL; NICKEL;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 33947718744     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.02.015     Document Type: Article

References (64)

1. Reviews:. Noyori R., and Kitamura M. Angew. Chem., Int. Ed. Engl. 30 (1991) 49-69
2. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), Wiley, New York Chapter 5
3. Soai K., and Niva S. Chem. Rev. 92 (1992) 833-856
4. Pu L., and Yu H.-B. Chem. Rev. 101 (2001) 757-824
5. Reviews:. Alexakis A., and Benhaim C. Eur. J. Org. Chem. (2002) 3221
6. Krause N., and Roder A.H. Synthesis (2001) 171
7. Sibi M.P., and Manyem S. Tetrahedron 56 (2000) 8033
8. Feringa B.L. Acc. Chem. Res. 33 (2000) 346
9. Krause N. Angew. Chem., Int. Ed. 37 (1998) 283
10. Selected examples:. Liu L.-T., Wang M.-C., Zhao W.-X., Zhou Y.-L., and Wang X.-D. Tetrahedron: Asymmetry 17 (2006) 136
11. Takahashi Y., Yamamoto Y., Katagiri K., Danjo H., Yamaguchi K., and Imamoto T. J. Org. Chem. 70 (2005) 9009
12. Alexakis A., Polet D., Rosset S., and March S. J. Org. Chem. 69 (2004) 5660
13. Scafato P., Labano S., Cunsolo G., and Rosini C. Tetrahedron: Asymmetry 14 (2003) 3873
14. Liang Y., Gao S., Wan H., Hu Y., Chen H., Zheng Z., and Hu X. Tetrahedron: Asymmetry 14 (2003) 3211
15. Hu Y., Liang X., Wang J., Zheng Z., and Hu X. J. Org. Chem. 68 (2003) 4542
16. Iuliano A., and Scafato P. Tetrahedron: Asymmetry 14 (2003) 611
17. Zhou H., Wang W.-H., Fu Y., Xie J.-H., Shi W.-J., Wang L.-X., and Zhou Q.-L. J. Org. Chem. 68 (2003) 1582
18. Shintani R., and Fu G.C. Org. Lett. 4 (2002) 3699
19. Reetz M.T., Gosberg A., and Moulin D. Tetrahedron Lett. 43 (2002) 1189
20. Martorell A., Naasz R., Feringa B.L., and Pringle P.G. Tetrahedron: Asymmetry 12 (2001) 2497
21. Hu X., Chen H., and Zhang X. Angew. Chem., Int. Ed. 38 (1999) 3518
22. Alexakis A., Vastra J., Burton J., Benhaim C., and Mangeney P. Tetrahedron Lett. 39 (1998) 7869
23. Selected examples:. Bolm C., Ewald M., and Felder M. Chem. Ber. 125 (1992) 1205
24. Bolm C. Tetrahedron: Asymmetry 2 (1991) 701
25. Jansen J.F.G.A., and Feringa B.L. Tetrahedron: Asymmetry 3 (1992) 581
26. de Vries A.H.M., Jansen J.F.G.A., and Feringa B.L. Tetrahedron 50 (1994) 4479
27. Uemura M., Miyake R., Nakayama K., and Hayashi Y. Tetrahedron: Asymmetry 3 (1992) 713
28. Asami M., Usui K., Higuchi S., and Inoue S. Chem. Lett. (1994) 297
29. Spieler J., Huttenloch O., and Waldmann H. Eur. J. Org. Chem. (2000) 391
30. Wakimoto I., Tomioka Y., and Kawanami Y. Tetrahedron 58 (2002) 8095
31. Wang H.-S., Da C.-S., Xin Z.-Q., Su W., Xiao Y.-N., Liu D.-X., and Wang R. Chin. J. Chem. 21 (2003) 1105
32. Unaleroglu C., Aydin A.E., and Demir A.S. Tetrahedron: Asymmetry 17 (2006) 742
33. Yamashita M., Yamada K., and Tomioka K. Org. Lett. 7 (2005) 2369
34. Cobb A.J.A., and Marson C.M. Tetrahedron 61 (2005) 1269
35. Tanner D., Korno H.T., Gujarro D., and Andersson P.G. Tetrahedron 54 (1998) 14213
36. Lawrence C.F., Nayak S.K., Thijs L., and Zwanenburg B. Synlett (1999) 1571
37. Holte P., Wijgergangs J.-P., Thijs L., and Zwanenburg B. Org. Lett. 1 (1999) 1095
38. Wang M.-C., Liu L.-T., Zhang J.-S., Shi Y.-Y., and Wang D.-K. Tetrahedron: Asymmetry 15 (2004) 3853
39. Wang M.-C., Wang D.-K., Zhu Y., Liu L.-T., and Guo Y.-F. Tetrahedron: Asymmetry 15 (2004) 1289
40. Wang M.-C., Hou X.-H., Xu C.-L., Liu L.-T., Li G.-L., and Wang D.-K. Synthesis (2005) 3620
41. Wang M.-C., Hou X.-H., Chi C.-X., and Tang M.-S. Tetrahedron: Asymmetry 17 (2006) 2126
42. Shi M., Jiang J.-K., and Feng Y.-S. Tetrahedron: Asymmetry 11 (2000) 4923
43. Page P.C.B., Allin S.M., Maddocks S.J., and Elsegood M.R.J. J. Chem. Soc., Perkin Trans. 1 36 (2002) 2827
44. Shadakshari U., and Nayak S.K. Tetrahedron 57 (2001) 8185
45. Dogan O., Koyuncu H., Garner P.P., Bulut A., Youngs W., and Panzner M. Org. Lett. 8 (2006) 4687
46. Dogan, Ö.; Bulut, A.; Aslan, A.; Izgü, E. C., unpublished results.
47. 2 = Fc) see:. Dogan O., Şenol V., Zeytinci S., Koyuncu H., and Bulut A. J. Organomet. Chem. 690 (2005) 430
48. Vogel's Textbook of Practical Organic Chemistry (ELBS). 5th ed. (1989), Longman, UK p 1034
49. Pitts M.R., Harrison J.R., and Moody C.J. J. Chem. Soc, Perkin Trans. 1 (2001) 955
50. Solcaniova E., and Toma S. Org. Mag. Res. 14 (1980) 138
51. Hino K., Nagai Y., Uno H., Masuda Y., Oka M., and Karasawa T. J. Med. Chem. 31 (1988) 107
52. Xian H., Linghong X., and Hong I.N. J. Org. Chem. 53 (1988) 4862
53. Huang J., and Huang Y.-Z. J. Organomet. Chem. 414 (1991) 49
54. Noyce D.S., and Jorgenson M.J. J. Am. Chem. Soc. 84 (1962) 4312
55. Ranu B.C., and Jana R. J. Org. Chem. 70 (2005) 8621
56. Lopez S.N., Castelli M.V., Zacchino S.A., Dominguez J.N., Lobo G., Charris-Charris J., Cortes J.C.G., Ribas J.C., Devia C., Rodriguez A.M., and Enriz R.D. Bioorg. Med. Chem. 9 (2001) 1999
57. Peach P., Cross D.J., Kenny J.A., Mann I., Houson I., Campbell L., Walsgroveb T., and Wills M. Tetrahedron 62 (2006) 1864
58. Concello J.M., Bernad P.L., Huerta M., Garcia-Granda S., and Diaz M.R. Chem. Eur. J. 9 (2003) 5343
59. Huang D., Wang J.-X., Hu Y., Zhang Y., and Tang J. Synth. Commun. 32 (2002) 971
60. Wu J., Zhang D., and Wei S. Synth. Commun. 35 (2005) 1213
61. Wan H., Hu Y., Liang Y., Gao S., Wang J., Zheng Z., and Hu X. J. Org. Chem. 68 (2003) 8277
62. Brienne M.J., Ouannes J., and Jacques J. Bull. Chem. Soc. Chim. Fr. (1967) 613
63. Cramer N., Laschat S., and Baro A. Organometallics 25 (2006) 2284
64. Soai K., Yokoyama S., Hayasaka T., and Ebihara K. J. Org. Chem. 53 (1988) 4149