Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): Design, synthesis, application and characteristics in catalytic asymmetric aziridination

Tetrahedron Asymmetry

Volumn 16, Issue 22, 2005, Pages 3718-3734

  Ma, Linge ^a   Jiao, Peng ^a   Zhang, Qihan ^a   Xu, Jiaxi ^a  

^a Peking University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ANTHRACENE DERIVATIVE; BENZENE DERIVATIVE; CHALCONE DERIVATIVE; IODINE DERIVATIVE; LEWIS BASE; LIGAND; OXAZOLINE DERIVATIVE; OXYGEN; TOLUENE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; COMPARATIVE STUDY; ELECTRON; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 27944489609     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.09.025     Document Type: Article

References (54)

1. For recent reviews on the application of chiral bis(oxazoline)-metal complexes in catalytic asymmetric reactions, see: A. Pfaltz Acc. Chem. Res. 26 1993 339 345
2. A.K. Ghosh, P. Mathivanan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1 45
3. H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151 4202
4. A.V. Bedekar, E.B. Koroleva, and P.G. Andersson J. Org. Chem. 62 1997 2518 2526
5. Asymmetric aziridination catalyzed by bis-oxazoline copper complexes, see: D.A. Evans, K.A. Woerpel, M.M. Hinman, and M.M. Faul J. Am. Chem. Soc. 113 1991 726 728
6. D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes J. Am. Chem. Soc. 115 1993 5328 5329
7. A.E. Hatimi, M. Gómez, S. Jansat, G. Muller, M. Font-Bardía, and X. Solans J. Chem. Soc., Dalton Trans. 1998 4229 4236
8. For a recent review on the synthesis and application of pyridine-2,6-bis(oxazolines), see: G. Desimoni, G. Faita, and P. Quadrelli Chem. Rev. 103 2003 3119 3154
9. S. Kanemasa, Y. Oderaotoshi, H. Yamamoto, J. Tanaka, E. Wada, and D.P. Curran J. Org. Chem. 62 1997 6454 6455
10. A. Voituriez, and E. Schulz Tetrahedron: Asymmetry 14 2003 339 346
11. T. Suzuki, K. Kinoshita, H. Kawada, and M. Nakada Synlett 2003 570 572
12. M. Inoue, T. Suzuki, and M. Nakada J. Am. Chem. Soc. 125 2003 1140 1141
13. J.M. Takacs, D.A. Quincy, W. Shay, B.E. Jones, and C.R. Ross II Tetrahedron: Asymmetry 8 1997 3079 3087
14. D.M. Du, B. Fu, and W.T. Hua Tetrahedron 59 2003 1933 1938
15. P. Jiao, J.X. Xu, Q.H. Zhang, M.C.K. Choi, and A.S.C. Chan Tetrahedron: Asymmetry 12 2001 3081 3088
16. K.B. Lipkowitz, and M. Pradhan J. Org. Chem. 68 2003 4648 4656
17. For recent reviews on the asymmetric aziridination, see: E.N. Jacobsen E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 2 1999 Springer Berlin 607
18. P. Muller, and C. Fruit Chem. Rev. 103 2003 2905 2920
19. A.H. Li, L.X. Dai, and A.K. Aggarwcal Chem. Rev. 97 1997 2341 2372
20. Asymmetric aziridination catalyzed by diimine copper complexes, see: Z. Li, K.R. Cosner, and E.N. Jacobsen J. Am. Chem. Soc. 115 1993 5326 5327
21. Z. Li, R.W. Quan, and E.N. Jacobsen J. Am. Chem. Soc. 117 1995 5889 5890
22. R.W. Quan, Z. Li, and E.N. Jacobsen J. Am. Chem. Soc. 118 1996 8156 8157
23. K.M. Gillespie, C.J. Sanerd, P. O'Shaughnessy, I. Westmoreland, P. Thickitt, and C.P. Scott J. Org. Chem. 67 2002 3450 3458
24. M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu J. Org. Chem. 67 2002 2101 2110
25. K.B. Hansen, N.S. Finnney, and E.N. Jacobsen Angew. Chem., Int. Ed. Engl. 34 1995 676 678
26. K. Juhl, R.G. Hazell, and K.A. Jorgensen J. Chem. Soc., Perkin. Trans. 1 1999 2293 2297
27. P. Brandt, M.J. Sodergren, P.G. Andersson, and P.-O. Norrby J. Am. Chem. Soc. 122 2000 8013 8020
28. A.K. Aggarwal, and J.L. Templeton J. Org. Chem. 61 1996 8368 8369
29. D.K. Wang, L.X. Dai, and X.L. Hou Chem. Commun. 1997 1231 1232
30. J.X. Xu, L.G. Ma, and P. Jiao Chem. Commun. 2004 1616 1617
31. Y. Imai, W.B. Zhang, T. Kida, Y. Nakatsuji, and I. Ikeda Tetrahedron: Asymmetry 7 1996 2453 2462
32. M.E. Rogers, and A.I. Averill J. Org. Chem. 51 1986 3308 3314
33. H. Waldmann, and R. Stengl Chem. Ber. 83 1950 167 170
34. A.H. Beckett, and J. Walker Tetrahedron 19 1963 545 556
35. M.B. Andrus, and D. Asgari Tetrahedron 56 2000 5775 5780
36. P. Muller, and C. Fruit Chem. Rev. 103 2003 2905
37. H. Suga, A. Kakehi, T. Ibata, T. Fudo, Y. Watanabe, and Y. Kinoshita Bull. Chem. Soc. Jpn. 76 2003 189 199
38. P. Muller, G. Bernardinelli, Y.F. Allenbach, M. Ferri, and H.D. Flack Org. Lett. 6 2004 1725 1728
39. N. Isaacs Physical Organic Chemistry 2nd ed. 1995 Addison Wesley Longman Essex, England p 152
40. J.X. Xu, T.Z. Wei, and Q.H. Zhang J. Org. Chem. 69 2004 6860 6866
41. T. Saito, M. Sakairi, and D. Akiba Tetrahedron Lett. 42 2001 5451 5454
42. D.A. Alonso, and P.G. Andersson J. Org. Chem. 63 1998 9455 9461
43. V.K. Aggarwal, A. Thompson, R.V.H. Jones, and M.C.H. Standen J. Org. Chem. 61 1996 8368 8369
44. K.M. Gillespie, E.J. Crust, R.J. Deeth, and P. Scott Chem. Commun. 2001 785 786
45. Y. Wang, and K.L. Ding J. Org. Chem. 66 2001 3238 3241
46. G.I. Geory, G.C.B. Harriman, and S.A. Peterson J. Org. Chem. 60 1995 7366 7368
47. N. Fujii, K. Nakai, H. Habashita, Y. Hotta, H. Tamamura, A. Otaka, and T. Ibuka Chem. Pharm. Bull. 42 1994 2241 2250
48. G.A. Olah, B.G.B. Gupta, S.C. Narang, and R. Malhotra J. Org. Chem. 44 1979 4272 4275
49. J.M. Klunder, T. Onami, and K.B. Sharpless J. Org. Chem. 54 1989 1295 1304
50. For a recent review on ring-opening reactions of unsymmetric aziridines with nucleophiles, see: L.G. Ma, and J.X. Xu Prog. Chem. (Huaxue Jinzhan) 16 2004 220 235
51. For a recent review on the π stacking interaction in asymmetric synthesis, see: G.B. Jones, and B. Chapman Synthesis 1995 475 497
52. P. Dauban, and P.R.H. Dodd Org. Lett. 2 2000 2327 2329
53. L.G. Ma, D.M. Du, and J.X. Xu J. Org. Chem 70 2005 10155 10158
54. S.L. Ali, M.D. Nikalje, and A. Sudalai Org. Lett. 1 1999 705 707