Catalytic asymmetric addition of alkynylzinc reagents to ketones using polymer-supported chiral Schiff-base amino alcohols

Tetrahedron Asymmetry

Volumn 19, Issue 2, 2008, Pages 191-196

  Chen, Chao ^a,b   Hong, Liang ^a   Zhang, Bangzhi ^a   Wang, Rui ^a,b  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AMINOALCOHOL; KETONE DERIVATIVE; LIGAND; POLYMER; REAGENT; SCHIFF BASE; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RECYCLING;

EID: 39049155381     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.11.040     Document Type: Article

References (67)

1. Forrat V.J., Ramón D.J., and Yus M. Tetrahedron: Asymmetry 17 (2006) 2054-2058
2. Altava B., Burguete M.I., Escuder B., Luis S.V., Salvador R.V., Fraile J.M., Mayoral J.A., and Royo A.J. J. Org. Chem. 62 (1997) 3126
3. Yang X.W., Sheng J.H., Da C.S., Wang H.S., Su W., Wang R., and Chan A.S.C. J. Org. Chem. 65 (2000) 295
4. Yang X.W., Su W., Liu D.X., Wang H.S., Sheng J.H., Da C.S., Wang R., and Chan A.S.C. Tetrahedron 56 (2000) 3511
5. Vidal-Ferran A., Bampos N., Moyano A., Pericàs M.A., Riera A., and Sanders J.K.M. J. Org. Chem. 63 (1998) 6309
6. Fan Q.H., Li Y.M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
7. Leadbeater N.E., and Marco M. Chem. Rev. 102 (2002) 3217
8. Pu L. Tetrahedron: Asymmetry 9 (1998) 1457
9. Holte P.t., Wijgergangs J.-P., Thijs L., and Zwanenburg B. Org. Lett. 1 (1999) 1095
10. Hui X.X., Chen C.A., Wu K.H., and Gau H.M. Chirality 19 (2007) 10-15
11. Fraile J.M., Mayoral J.A., Serrano J., Pericàs M.A., Solà L., and Castellnou D. Org. Lett. 5 (2003) 4333-4335
12. Pu L. Chem. Eur. J. 5 (1999) 2227-2232
13. Sellner H., and Seebach D. Angew. Chem., Int. Ed. 38 (1999) 1918-1920
14. Sellner H., Faber C., Rheiner P.B., and Seebach D. Chem. Eur. J. 6 (2000) 3692-3705
15. Abramson S., Laspéras M., Galarneau A., Desplantier-Giscand D., and Brunel D. Chem. Commun. (2000) 1773-1774
16. Selected references on the enantioselective alkynylation of aldehydes. Pu L. Tetrahedron 59 (2003) 9873
17. Cozzi P.G., Hilgraf R., and Zimmermann N. Eur. J. Org. Chem. (2004) 4095
18. Anand N.K., and Carreira E.M. J. Am. Chem. Soc. 123 (2001) 9687
19. Frantz D., Fassler E.R., and Carreira E.M. J. Am. Chem. Soc. 122 (2000) 1806
20. Lu G., Li X., Chan W.L., and Chan A.S.C. Chem. Commun. (2002) 172
21. Li X., Lu G., Kwok W.H., and Chan A.S.C. J. Am. Chem. Soc. 124 (2002) 12636
22. Boyall D., Frantz D.E., and Carreira E.M. Org. Lett. 4 (2002) 2605
23. Moore D., and Pu L. Org. Lett. 4 (2002) 1855
24. Gao G., Moore D., Xie R.G., and Pu L. Org. Lett. 4 (2002) 4143
25. Gao G., Xie R.G., and Pu L. Proc. Nat. Acad. Sci. 101 (2004) 5417
26. Takita R., Yakura K., Ohshima T., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 13760
27. Gao G., Wang Q., Yu X.Q., Xie R.G., and Pu L. Angew. Chem., Int. Ed. 45 (2006) 122
28. Trost B.M., Weiss A.H., and Wangelin J.V. J. Am. Chem. Soc. 128 (2006) 8
29. Emmerson D.P.G., Hems W.P., and Davis B.G. Org. Lett. 8 (2006) 207
30. Yamashita M., Yamada K.-i., and Tomioka K. Adv. Synth. Catal. 347 (2005) 1649-1652
31. Cozzi P.G. Angew. Chem., Int. Ed. 42 (2003) 2895
32. Cozzi P.G., and Alesi S. Chem. Commun. (2004) 2448
33. Lu G., Li X.S., Jia X., Chan W.L., and Chan A.S.C. Angew. Chem., Int. Ed. 42 (2003) 5057
34. Lu G., Li X.S., Li Y.M., Kwong F.Y., and Chan A.S.C. Adv. Synth. Catal. 348 (2006) 1926-1933
35. Saito B., and Katsuki T. Synlett (2004) 1557
36. Jiang B., and Feng Y. Tetrahedron Lett. 43 (2002) 2975-2977
37. Forrat V.J., Ramón D.J., and Yus M. Tetrahedron: Asymmetry 16 (2005) 3341-3344
38. Mao J.C., Wan B.S., Wu F., and Lu S.W. J. Mol. Catal. A: Chem. 237 (2005) 126-131
39. Cai H.Q., Chen C., Liu L., Ni J.M., and Wang R. J. Mol. Catal. A: Chem. 253 (2006) 86
40. Forrat V.J., Prieto O., Ramón D.J., and Yus M. Chem. Eur. J. 12 (2006) 4431-4445
41. Cozzi P.G., Hilgraf R., and Zimmermann N. Eur. J. Org. Chem. (2004) 4095
42. Ramón D.J., and Yus M. Angew. Chem., Int. Ed. 43 (2004) 284-287
43. Degni S., Wilén C.E., and Lei{dotless}́no R. Tetrahedron: Asymmetry 15 (2004) 231-237
44. Itsuno S., and Frechet J.M.J. J. Org. Chem. 52 (1987) 4140
45. Hodge P., Sung D.W.L., and Stratford P.W. J. Chem. Soc., Perkin Trans. 1 (1999) 2335
46. Kleijin H., Rijinberg E., Jastrzebski Johann.T.B.H., and van Koten G. Org. Lett. 1 (1999) 835
47. Soai K., Niwa S., and Watanabe M. J. Org. Chem. 53 (1988) 927
48. Anyanwu U.K., and Venkataraman D. Tetrahedron Lett. 44 (2003) 6445
49. Soai K., and Niwa S. Chem. Rev. 92 (1992) 833-856
50. Pericàs M.A., Rodríguez I., Riera A., and Solà L. Adv. Synth. Catal. 345 (2003) 1305
51. Castellnou D., Fontes M., Jimeno C., Font D., Solà L., Verdaguer X., and Pericas M.A. Tetrahedron 61 (2005) 12111
52. Castellnou D., Solà L., Jimeno C., Fraile J.M., Mayoral J.A., Riera A., and Pericàs M.A. J. Org. Chem. 70 (2005) 433
53. Laspéras M., Bellocq N., Brunel D., and Moreau P. Tetrahedron: Asymmetry 9 (1998) 3053
54. Bellocq N., Abramson S., Laspéras M., Brunel D., and Moreau P. Tetrahedron: Asymmetry 10 (1999) 3229
55. Ding K.L., Wang Z., Wang X.W., Liang Y.X., and Wang X.S. Chem. Eur. J. 12 (2006) 5188-5197
56. Pathak K., Bhatt A.P., Abdi S.H.R., Kureshy R.I., Khan N.-U., Ahmad K.I., and Jasra R.V. Chirality 19 (2007) 82-88
57. Selected recent examples of our group:. Kang Y.F., Liu L., Wang R., Zhou Y.F., and Yan W.J. Adv. Synth. Catal. 347 (2005) 243
58. Zhou Y.F., Wang R., Xu Z.Q., Yan W.J., Liu L., Kang Y.F., and Han Z.J. Org. Lett. 6 (2004) 4147
59. Liu L., Wang R., Kang Y.F., Chen C., Xu Z.Q., Zhou Y.F., Ni M., Cai H.Q., and Gong M.Z. J. Org. Chem. 70 (2005) 1084
60. Chen C., Hong L., Xu Z.Q., Liu L., and Wang R. Org. Lett. 8 (2006) 2277
61. Wang Q., Zhang B.Z., Hu G.W., Chen C., Zhang Q.Y., and Wang R. Org. Biomol. Chem. 5 (2007) 1161-1163
62. Lin L., Jiang X.X., Liu W.X., Qiu L., Xu Z.Q., Xu J.K., Chan A.S.C., and Wang R. Org. Lett. 9 (2007) 2329-2332
63. Cai H.Q., Chen C., Liu L., Ni J.M., and Wang R. J. Mol. Catal. A: Chem. 253 (2006) 86
64. Ni M., Wang R., Han Z.J., Mao B., Da C.S., Liu L., and Chen C. Adv. Synth. Catal. 347 (2005) 1659
65. When dichloromethane was used for the reaction, the polymer became stuck on the inner wall of the round-bottomed flask upon stirring. However when hexane and toluene were used as solvents, the appearance disappeared.
66. 2Zn/phenylacetylene/ketones = 0.1:2:2:1, 39% ee, yield 81%).
67. Cozzi P.G., Rudolph J., Bolm C., Norrby P.O., and Tomasini C. J. Org. Chem. 70 (2005) 5733