Synthesis of novel C2-symmetric chiral bis(oxazoline) ligands and their application in the enantioselective addition of diethylzinc to aldehydes

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 119-126

  Fu, Bin ^a   Du, Da Ming ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; DIETHYLZINC; HYDROXYL GROUP; LIGAND; OXAZOLINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0347418209     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.11.006     Document Type: Article

References (62)

1. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley, New York.
2. (a) Noyori R., Kitamura M. Angew. Chem., Int. Ed. Engl. 30:1991;49-69
3. (b) Soai K., Niwa S. Chem. Rev. 92:1992;833
4. (c) Pu L., Yu H.B. Chem. Rev. 101:2001;757-824.
5. (a) Schmidt B., Seebach D. Angew Chem., Int. Ed. Engl. 30:1991;99-101
6. (b) Schmidt B., Seebach D. Angew. Chem., Int. Ed. Engl. 30:1991;1321-1323
7. (c) Weber B., Seebach D. Tetrahedron. 50:1994;7473-7478
8. (d) Ito Y.N., Ariza X., Beck A.K., Bohác A., Ganter C., Gawley R.E., Kuhnle F.N.M., Tuleja J., Wang Y.M., Seebach D. Helv. Chim. Acta. 77:1994;2071-2210
9. (e) Seebach D., Beck A.K., Schmidt B., Wang Y.M. Tetrahedron. 50:1994;4363-4384.
10. (a) Pu L. Chem. Rev. 98:1998;2405-2494
11. (b) Mori M., Nakai T. Tetrahedron Lett. 38:1997;6233-6236
12. (c) Zhang F.Y., Yip C.W., Cao R., Chan A.S.C. Tetrahedron: Asymmetry. 8:1997;585-589
13. (d) Davis T.J., Balsells J., Carroll P.J., Walsh P.J. Org. Lett. 3:2001;2161-2164
14. (e) Huang W.S., Hu Q.S., Pu L. J. Org. Chem. 64:1999;7940
15. (f) Chen Y., Yekta S., Martyn L.J.P., Zheng J., Yudin A.K. Org. Lett. 2:2000;3433-3436
16. (g) Shen X.Q., Guo H., Ding K.L. Tetrahedron: Asymmetry. 11:2000;4321-4327.
17. (a) Hof R.P., Poelert M.A., Peper N.C.M.W., Kellogg R.M. Tetrahedron: Asymmetry. 5:1994;31-34
18. (b) Kang J., Lee J.W., Kim J.I. J. Chem. Soc., Chem. Commun. 1994;2009-2010.
19. (a) Cozzi P.G., Papa A., Umani-Ronchi A. Tetrahedron Lett. 37:1996;4613
20. (b) Mino T., Oishi K., Yamashita M. Synlett. 1998;965-966
21. (c) Fleischer R., Braun M. Synlett. 1998;1441-1443.
22. (a) Bauer T., Tarasiuk J., Paśniczek K. Tetrahedron: Asymmetry. 13:2002;77-82
23. (b) Cho B.T., Chun Y.S., Yang W.K. Tetrahedron: Asymmetry. 11:2002;2149-2157
24. (c) Cho B.T., Kim N. J. Chem. Soc., Perkin Trans. 1. 1996;2901-2907.
25. (a) Royo E., Betancort J.M., Davis T.J., Caroll P., Walsh P.J. Organometallics. 19:2000;4840-4851
26. (b) Paquette L.A., Zhou R. J. Org. Chem. 64:1999;7929-7934
27. (c) Hwang C.D., Uang B.J. Tetrahedron: Asymmetry. 54:1998;8275-8319
28. (d) Knochel P., Perea J., Almena J., Jones P. Tetrahedron. 54:1998;8275-8319
29. (e) Guo C., Qiu J., Zhang X., Verduge D., Larter M.L., Christie R., Kenney P., Walsh P.J. Tetrahedron. 53:1997;4145-4158.
30. Shi M., Sui W.S. Tetrahedron: Asymmetry. 10:1999;3319-3325.
31. (a). For reviews: Ghosh A.K., Mathivanan P., Cappiello J. Tetrahedron: Asymmetry. 9:1998;1-45 (b) Johnson J.S., Evans D.A. Acc. Chem. Res. 33:2000;325.
32. (a). For reviews: Ghosh A.K., Mathivanan P., Cappiello J. Tetrahedron: Asymmetry. 9:1998;1-45
33. (b) Johnson J.S., Evans D.A. Acc. Chem. Res. 33:2000;325.
34. (a) Chan T.H., Zheng G.Z. Can. J. Chem. 75:1997;629-633
35. (b) Zhu H.J., Zhao B.T., Dai W.M., Zhou J., Hao X.J. Tetrahedron: Asymmetry. 9:1998;2879-2888
36. (c) Shintani R., Fu G.C. Org. Lett. 4:2002;3699-3702.
37. (a) Allen J.V., Frost C.G., Williams J.M.J. Tetrahedron: Asymmetry. 4:1993;649-650
38. (b) Deng W.P., Hou X.L., Dai L.X. Tetrahedron: Asymmetry. 10:1999;4689-4693.
39. (a) Zhang W.B., Yoshinaga H., Imai Y., Kida T., Nakatsuji Y., Ikeda I. Synlett. (10):2000;1512-1514;
40. (b) Imai Y., Matsuo S., Zhang W.B., Nakatsuji Y., Ikeda I. Synlett. (2):2000;239-241.
41. (a) Bolm C., Muniz-fernandez K., Seger A., Raabe G., Gunther J. J. Org. Chem. 63:1998;7860-7867;
42. (b) Bolm C., Muniz-fernandez K., Hildebrand J.P. Org. Lett. 1:1998;491-493.
43. Pastor I.M., Adolfsson H. Tetrahedron Lett. 43:2002;1743-1746.
44. (a) Du D.M., Wang Z.Y., Xu D.C., Hua W.T. Synthesis. 2002;2347-2352;
45. (b) Wang Z.Y., Du D.M., Wu D., Hua W.T. Synth. Commun. 33:2003;1275-1283;
46. (c) Xu D.C., Du D.M., Ji N., Wang Z.Y., Hua W.T. Synth. Commun. 33:2003;2563-2574.
47. (a) Du D.M., Fu B., Hua W.T. Tetrahedron. 59:2003;1933-1938;
48. (b) Fu B., Du D.M. Chin. J. Chem. 21:2003;597-599.
49. (a) Kenner J. J. Chem. Soc. 1913;613-627;
50. (b) Dvorken L.V., Smyth R.B., Mislow K. J. Am. Chem. Soc. 80:1958;486-492.
51. Denmark S.E., Nakajima N., Nicaise O.J.C., Faucher A.M., Edwards J.P. J. Org. Chem. 60:1995;4884-4892.
52. Phillips A.J., Uto Y., Wipf P., Reno M.J., Williams D.R. Org. Lett. 2:2000;1165-1168.
53. (a) Mazaleyrat J.P., Gaucher A., Savrda J., Wakselman M. Tetrahedron: Asymmetry. 8:1997;619-631;
54. (b) Gaucher A., Bintein F., Wakselman M., Mazaleyrat J.P. Tetrahedron Lett. 39:1998;575-578.
55. (a) Kitamura M., Suga S., Kawai K., Noyori R. J. Am. Chem. Soc. 108:1986;6071-6072;
56. (b) Jin M.J., Ahn S.J., Lee K.S. Tetrahedron Lett. 37:1996;8767-8770;
57. (c) Watanabe M. Tetrahedron Lett. 36:1995;8991-8994;
58. (d) Sola L., Reddy K.S., Vidal-Ferran A., Moyano A., Pericas M.A., Riera A., Alvarez-Larena A., Piniella J.F. J. Org. Chem. 63:1998;7078-7082
59. (e) Dai W.M., Zhu H.J., Hao X.J. Tetrahedron: Asymmetry. 11:2000;2315-2337;
60. (f) Cardellicchio C., Ciccarella G., Naso F., Perna F., Tortorella P. Tetrahedron. 55:1999;14685-14692.
61. (a) Itsumo S., Frechet J.M.J. J. Org. Chem. 52:1987;4140;
62. (b) Ko D.H., Kim K.H., Ha D.C. Org. Lett. 4:2002;3759-3762.