Linear polystyrene anchored l-proline, new recyclable organocatalysts for the aldol reaction in the presence of water

Tetrahedron Asymmetry

Volumn 18, Issue 22, 2007, Pages 2649-2656

  Liu, Yu Xia ^a   Sun, Ya Nan ^a   Tan, Hao Han ^a   Liu, Wei ^a   Tao, Jing Chao ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; POLYSTYRENE; PROLINE; WATER;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; FILTRATION; PRECIPITATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 36448943539     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.10.032     Document Type: Article

References (60)

1. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395-2396
2. List B. Acc. Chem. Res. 37 (2004) 548-557
3. Satio S., and Yamamoto H. Acc. Chem. Res. 37 (2004) 570-579
4. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580-591
5. In: Dalko P.I. (Ed). Enantioselective Organocatalysts (2007), Wiley-VCH
6. Berkessel A., and Groeger H. Asymmetric Organocatalysts (2005), Wiley-VCH
7. Palomo C., Oiarbide M., and Garcia J.M. Chem. Soc. Rev. 33 (2004) 65-75
8. Alcaide B., and Almendros P. Eur. J. Org. Chem. (2002) 1595-1601
9. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
10. Vidal-Ferran A., Bampos N., Moyano A., Pericàs M.A., Riera A., and Sanders J.K.M. J. Org. Chem. 63 (1998) 6309-6318
11. Pericàs M.A., Castellnou D., Rodríguez I., Riera A., and Solà L. Adv. Synth. Catal. 345 (2003) 1305-1313
12. Castellnou D., Solà L., Jimeno C., Fraile J.M., Moyoral J.A., Riera A., and Pericàs M.A. J. Org. Chem. 70 (2005) 433-438
13. Castellnou D., Fontes M., Jimeno C., Font D., Solà L., Verdaguer X., and Pericàs M.A. Tetrahedron 61 (2005) 12111-12120
14. Shen Z.-X., Chen W.-H., Jiang H., Ding Y., Luo X.-Q., and Zhang Y.-W. Chirality 17 (2005) 119-120
15. Bellis E., and Kokotos G. Tetrahedron 61 (2005) 8669-8676
16. Berkessel A., Koch B., and Lex J. Adv. Synth. Catal. 346 (2004) 1141-1146
17. Hartikka A., and Arvidsson P.I. Tetrahedron: Asymmetry 15 (2004) 1831-1834
18. Nakadai M., Saito S., and Yamamoto H. Tetrahedron 58 (2002) 8167-8177
19. Kano T., Takai J., Tokuda O., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 3055-3057
20. Kano T., Tokuda O., and Maruoka K. Tetrahedron Lett. 47 (2006) 7423-7426
21. Shi L.-X., Sun Q., Ge Z.-M., Zhu Y.-Q., Cheng T.-M., and Li R.-T. Synlett (2004) 2215-2217
22. Mitsumori S., Zhang H., Cheong P.H.-Y., Houk K.N., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 1040-1041
23. Tang Z., Yang Z.-H., Chen X.-H., Cun L.-F., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. J. Am. Chem. Soc. 127 (2005) 9285-9289
24. Guizzetti S., Benaglia M., Raimondi L., and Celentano G. Org. Lett. 9 (2007) 1247-1250
25. Benaglia M., Celentano G., and Cozzi F. Adv. Synth. Catal. 343 (2001) 171-173
26. Benaglia M., Cinquini M., Cozzi F., Puglisis A., and Celentano G. Adv. Synth. Catal. 344 (2002) 533-542
27. Wu Y.-Y., Yu Y.-Z., Zhang M.-L., Zhao G., and Wang S.-W. Org. Lett. 8 (2006) 4417-4420
28. Andreae M.R.M., and Davis A.P. Tetrahedron: Asymmetry 16 (2005) 2487-2492
29. Akagawa K., Sakamoto S., and Kudo K. Tetrahedron Lett. 46 (2005) 8185-8187
30. Giacalone F., Gruttadauria M., Marculescu A.M., and Noto R. Tetrahedron Lett. 48 (2007) 255-257
31. Font D., Jimeno C., and Pericàs M.A. Org. Lett. 8 (2006) 4653-4655
32. Calderón F., Fernández R., Sánchez F., and Fernández-Mayoralas A. Adv. Synth. Catal. 347 (2005) 1395-1403
33. Kokotos G., and Bellis E.J. Mol. Catal. A: Chem. 241 (2005) 166-174
34. Gu L.-Q., Wu Y.-Y., Zang Y.-Z., and Zhao G. J. Mol. Catal. A: Chem. 263 (2007) 186-194
35. Liu, Y.-X.; Sun, Y.-N.; Tan, H.-H.; Tao, J.-C. Catal. Lett. 2007, doi:10.1007/s10562-007-9281-8.
36. Gruttadauria M., Riela S., Aprile C., Lo Meo P., D'Anna F., and Noto R. Adv. Synth. Catal. 348 (2006) 82-92
37. Loh T.-P., Feng L.-C., Yang H.-Y., and Yang J.-Y. Tetrahedron Lett. 43 (2002) 8741-8743
38. Córdova A. Tetrahedron Lett. 45 (2004) 3949-3952
39. Kitrusz P., Kmentova I., Gotov B., Toma S., and Solcaniova E. Chem. Commun (2002) 2510-2511
40. Lindstrom U.M. Chem. Rev 102 (2002) 2751-2772
41. Li C.-J. Chem. Rev 105 (2005) 3095
42. Pirrung M.C. Chem. Eur. J 12 (2006) 1312
43. Darbre T., and Machuqueiro M. Chem. Commun (2003) 1090-1091
44. Chimni S.S., Mahajan D., and Babu V.V.S. Tetrahedron Lett. 46 (2005) 5617-5619
45. Torii H., Nakadai M., Ishihara K., Saito S., and Yamamoto H. Angew. Chem., Int. Ed. 43 (2004) 1983-1986
46. Amedjkouh M. Tetrahedron: Asymmetry 16 (2005) 1411-1414
47. Fu Y.-Q., Li Z.-C., Ding L.-N., Tao J.-C., Zhang S.-H., and Tang M.-S. Tetrahedron: Asymmetry 17 (2006) 3351-3357
48. Hayashi Y., Sumiya T., Takahashi J., Gotoh H., Urushima T., and Shoji M. Angew. Chem., Int. Ed. 45 (2006) 958-961
49. Mase N., Nakai Y., Ohara N., Yoda H., Takabe K., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 734-735
50. Dziedzic P., Zou W., Hafren J., and Cordova A. Org. Biomol. Chem. 4 (2006) 38-40
51. Hayashi Y., Aratake S., Itoh T., Okano T., Sumiya T., and Shoji M. Chem. Commun (2007) 957-959
52. Hayashi Y. Angew. Chem., Int. Ed. 45 (2006) 8103-8104
53. Fu, Y.-Q.; Liu, Y.-X.; Tao, J.-C. Org. Biomol. Chem. 2007, submitted for publication.
54. Tamaki M., Han G., and Hruby V.J. J. Org. Chem. 66 (2001) 1038-1042
55. Ward D.V., and Jheengut V. Tetrahedron Lett. 45 (2004) 8347-8350
56. Tang Z., Yang Z.-H., Cun L.-F., Gong L.-Z., Mi A.-Q., and Jiang Y.-Z. Org. Lett. 6 (2004) 2285-2287
57. Ibrahem I., and Córdora A. Tetrahedron Lett. 46 (2005) 3363-3367
58. Nyborg A.I., Usano A., and Pihko P.M. Synlett (2004) 1891-1896
59. Brogan A.P., Dikerson T.J., and Janda K.D. Angew. Chem., Int. Ed. 45 (2006) 2-5
60. Rich D.H., and Gurwara S.K. J. Am. Chem. Soc. 107 (1975) 1575-1579