1,2,3-Triazole-linked dendrimers as a support for functionalized and recoverable catalysts for asymmetric borane reduction of prochiral ketones

Tetrahedron Asymmetry

Volumn 19, Issue 8, 2008, Pages 912-920

  Niu, Yan Ning ^a   Yan, Ze Yi ^b   Li, Gao Qiang ^a   Wei, Hai Long ^a   Gao, Guo Lin ^a   Wu, Lu Yong ^a   Liang, Yong Min ^a,c  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

^c LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; BORANE DERIVATIVE; DENDRIMER; KETONE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ELECTRON; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 43149091436     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.03.019     Document Type: Article

References (73)

1. Brunner H.J. Organomet. Chem. 500 (1995) 39-46
2. Hearshaw M.A., and Moss J.R. Chem. Commun. (1999) 1-8
3. Newkome G.R., He E., and Moorefield C.N. Chem. Rev. 99 (1999) 1689-1746
4. Hecht S., and Fréchet M.J. Angew. Chem., Int. Ed. 40 (2001) 74-91
5. Oosterom G.E., Reek J.N.H., Kamer P.C.J., and van Leeuwen P.W.N.M. Angew. Chem., Int. Ed. 40 (2001) 1828-1849
6. Astruc D., and Chardac F. Chem. Rev. 101 (2001) 2991-3024
7. Fan Q.-H., Li Y.-M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385-3466
8. Van Heerbeek R., Kamer P.C.J., van Leeuwen P.W.N.M., and Reek J.N.H. Chem. Rev. 102 (2002) 3717-3756
9. Bolm C., Derrien N., and Seger A. Chem. Commun. (1999) 2087-2088
10. Wang G.-y., Liu X.-Y., and Zhao G. Synlett (2006) 1150-1154
11. Moberg C. Angew. Chem., Int. Ed. 37 (1998) 248-268
12. Zhou J., and Tang Y. Chem. Soc. Rev. 34 (2005) 664-676
13. Kawasaki K., Tsumara S., and Katsuki T. Synlett (1995) 1245-1246
14. Kawasaki K., and Katsuki T. Tetrahedron 53 (1997) 6337-6350
15. Kohmura Y., and Katsuki K. Tetrahedron Lett. 41 (2000) 3941-3945
16. Kim S.G., and Ahn K.H. Tetrahedron Lett. 42 (2001) 4175-4177
17. Ahn K.H., Kim S.-G., Jung J., Kim K.-H., Kim J., Chin J., and Kim K. Chem. Lett. (2000) 170-171
18. Kim S.-G., Kim K.-H., Jung J., Shin S.K., and Ahn K.H. J. Am. Chem. Soc. 124 (2002) 591-596
19. Kim S.-G., Kim K.-H., Kim Y.K., Shin S.K., and Ahn K.H. J. Am. Chem. Soc. 125 (2003) 13819-13824
20. Gamble M.P., Smith A.R.C., and Wills M. J. Org. Chem. 63 (1998) 6068-6071
21. Foltz C., Stecker B., Marconi G., Bellemin-Laponnaz S., Wadepohl H., and Gade L.H. Chem. Commun. (2005) 5115-5117
22. Burns B., King N.P., Tye H., Studley J.R., Gamble M., and Wills M. J. Chem. Soc., Perkin Trans. (1998) 1027-1038
23. Tao F., Du D.-M., Lu S.-F., and Xu J. Org. Lett. 7 (2005) 2081-2084
24. Du D.-M., Tao F., Xu J., and Zhang S. Org. Lett. 8 (2006) 1327-1330
25. Singh V.K. Synthesis 7 (1992) 605-617
26. Deloux L., and Srebnik M. Chem. Rev. 93 (1993) 763-784
27. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1987-2012
28. Itsuno S. Organic Reactions Vol. 52 (1998), John Wiley, New York 395
29. Hirao A., Itsuno S., Nakahama N., and Yamazaki N. J. Chem. Soc., Chem. Commun. (1981) 315-317
30. Itsuno S., Ito K., Hirao A., Nakahama S., and Yamazaki N. J. Chem. Soc., Chem. Commun. (1983) 469-470
31. Itsuno S., and Ito K. J. Org. Chem. 49 (1984) 555-557
32. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551-5553
33. Corey E.J., and Reichard G.A. Tetrahedron Lett. 30 (1989) 5207-5210
34. Corey E.J., and Link J.O. Tetrahedron Lett. 33 (1992) 3431-3434
35. Corey E.J., and Helal C.J. Tetrahedron Lett. 36 (1995) 9153-9156
36. Helal C.J., Magriotis P.A., and Corey E.J. J. Am. Chem. Soc. 118 (1996) 10938-10939
37. Mathre S.A., Thompson A.W., Douglas K., Hoogsteen J.D., Carroll E.G., Corey E.J., and Grabowski J. J. Org. Chem. 58 (1993) 2880-2888
38. Quallich G.J., Blake J.F., and Woodall T.W. J. Am. Chem. Soc. 116 (1994) 8516-8525
39. Bach J., Berenger R., Gracia J., Loscertales T., and Vilarrasa J. J. Org. Chem. 61 (1996) 9021-9025
40. Price M.D., Sui J.K., Kurth M.J., and Schore N.E. J. Org. Chem. 67 (2002) 8086-8089
41. Xu J., Su X., and Zhang Q. Tetrahedron: Asymmetry 14 (2003) 1781-1786
42. Degni S., Wilen C.E., and Leino R. Tetrahedron: Asymmetry 15 (2004) 231-237
43. Yang G.Sh., Hu J.B., Zhao G., Ding Y., and Tang M.H. Tetrahedron: Asymmetry 10 (1999) 4307-4311
44. Hu J.-b., Zhao G., and Ding Z.-d. Angew. Chem., Int. Ed. 40 (2001) 1109-1111
45. Hu J.-b., Zhao G., Yang G.-s., and Ding Z.-d. J. Org. Chem. 66 (2001) 303-304
46. Gamble M.P., Smith A.R., and Wills M. J. Org. Chem. 63 (1998) 6068-6071
47. Li K.Y., Zhou Z.H., Wang L.X., Chen Q.F., Zhao G.F., Zhou Q.L., and Tang C.C. Tetrahedron: Asymmetry 14 (2003) 95-100
48. Zhang J., Zhou H.B., Liu S.M., Luo M.M., Xie R.G., Choi M.C.K., Zhou Z.Y., Chan A.S.C., and Yang T.K. Tetrahedron: Asymmetry 12 (2001) 1907-1912
49. Zhou H.B., Lü S.M., Xie R.G., Chan A.S.C., and Yang T.K. Tetrahedron Lett. 42 (2001) 1107-1110
50. Mase N., Watanabe K., Yoda H., Takabe K., Tanaka F., Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
51. Hawker C.J., and Wooley K.L. Science 309 (2005) 1200-1205
52. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
53. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
54. Lewis W.G., Green L.G., Grynszpan F., Radic Z., Carlier P.R., Taylor P., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 1053-1057
55. Himo F., Lovell T., Hilgraf R., Rostovtsev V.V., Noodleman L., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 210-216
56. Yan Z.-Y., Zhao Y.-B., Fan M.-J., Liu W.-M., and Liang Y.-M. Tetrahedron 61 (2005) 9331-9337
57. Zhao Y.-B., Yan Z.-Y., and Liang Y.-M. Tetrahedron Lett. 47 (2006) 1545-1549
58. Yan Z.-Y., Niu Y.-N., Wei H.-L., Wu L.-Y., Zhao Y.-B., and Liang Y.-M. Tetrahedron: Asymmetry 17 (2006) 3288-3293
59. Wu L.-Y., Yan Z.-Y., Xie Y.-X., Niu Y.-N., and Liang Y.-M. Tetrahedron: Asymmetry 18 (2007) 2086-2090
60. Li Y.W., Liu X.-Y., Yang Y.-Q., and Zhao G. J. Org. Chem. 72 (2007) 288-291
61. Xu J.X., Wei T.Z., and Zhang Q.H. J. Org. Chem. 68 (2003) 10146-10151
62. Xu J.X., Wei T.Z., and Zhang Q.H. J. Org. Chem. 69 (2004) 6860-6866
63. Xu J.X., Wei T.Z., and Zhang Q.H. Helv. Chim. Acta 88 (2005) 180-186
64. Wang X., Du J.-J., Liu H., Du D.-M., and Xu J.X. Heteroat. Chem. 18 (2007) 740-746
65. Du J.-J., Li Z.-Y., Du D.-M., and Xu J.X. J. Mol. Catal. A: Chem. 284 (2008) 40-45
66. Wu P., Feldman A.K., Nugent A.K., Hawker C.J., Scheel A., Voit B., Pyun J., Fréchet J.M.J., Sharpless K.B., and Fokin V.V. Angew. Chem., Int. Ed. 43 (2004) 3928-3932
67. Malkoch M., Schleicher K., Drockenmuller E., Hawker C.J., Russell T.P., Wu P., and Fokin V.V. Macromolecules 38 (2005) 3663-3678
68. Suseela K., and David G.C. J. Org. Chem. 61 (1996) 2511-2516
69. Cozzi P.G., and Kotrusz P. J. Am. Chem. Soc. 128 (2006) 4940-4941
70. Liu P.-N., Gu P.-M., Wang F., and Tu Y.-Q. Org. Lett. 6 (2004) 169-172
71. Basavaiah D., Jayapal Reddy G., and Venkateswara Rao K. Tetrahedron: Asymmetry 15 (2004) 1881-1888
72. Basavaiah D., Venkateswara Rao K., and Jayapal Reddy G. Tetrahedron: Asymmetry 17 (2006) 1036-1040
73. Gamble M.P., Smith A.R.C., and Wills M. J. Org. Chem. 63 (1998) 6068-6071