Enantioselective catalysis over chiral imidazolidin-4-one immobilized on siliceous and polymer-coated mesocellular foams

Advanced Synthesis and Catalysis

Volumn 348, Issue 15, 2006, Pages 2027-2032

  Zhang, Yugen ^a   Zhao, Lan ^a   Lee, Su Seong ^a   Ying, Jackie Y ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

Author keywords

Heterogeneous catalysis; Mesoporous materials; Organocatalysis; Polymer coating; Silica

Indexed keywords

EID: 33750527135     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600240     Document Type: Article

References (55)

1. Selected reviews: a) Special Issue about Asymmetric Organocatalysis (Eds.: K. N. Houk, B. List), Acc. Chem. Res. 2004, 37(8);
2. b) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138;
3. c) A. M. Rouhi, Chem. Eng. News 2004, 82, 41;
4. d) S. France, D. J. Guerin, S. J. Miller, T. Lectka, Chem. Rev. 2003, 103, 2985;
5. e) B. List, Tetrahedron 2002, 58, 5572;
6. f) M. Movassaghi, E. N. Jacobsen, Science 2002, 298, 1904;
7. g) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481;
8. h) H. Groger, J. Wilken, Angew. Chem. Int. Ed. 2001, 40, 529;
9. i) B. List, Synlett 2001, 1675.
10. a) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
11. b) A. Berkessel, H. Groger, Asymmetric Organocatalysis, VCH, Weinheim, 2004.
12. a) M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 2003, 103, 3401;
13. b) D. J. Cole-Hamilton, Science 2003, 299, 1702.
14. a) D. Zhao, J. Feng, Q. Huo, N. Melosh, G. H. Fredrickson, B. F. Chmelka, G. D. Stucky, Science 1998, 279, 548;
15. b) P. Schmidt-Winkel, W. W. Lukens, Jr., D. Zhao, P. Yang, B. F. Chmelka, G. D. Stucky, J. Am. Chem. Soc. 1999, 121, 254;
16. c) P. Schmidt-Winkel, W.W. Lukens, Jr., P. Yang, D. I. Margolese, J. S. Lettow, J. Y. Ying, G. D. Stucky, Chem. Mater. 2000, 12, 686;
17. d) J. S. Lettow, Y. J. Han, P. Schmidt-Winkel, P. Yang, D. Zhao, G. D. Stucky, J. Y. Ying, Langmuir 2000, 16, 8291;
18. e) J. S. Lettow, T. M. Lancaster, C. J. Glinka, J. Y. Ying, Langmuir 2005, 21, 5738.
19. a) T. M. Lancaster, S. S. Lee, J. Y. Ying, Chem. Commun. 2005, 3577;
20. b) S. S. Lee, S. Hadinoto, J. Y. Ying, Adv. Synth. Catal. 2006, 348, 1248;
21. c) S. S. Lee, J. Y. Ying, J. Mol. Catal. A: Chem. 2006, 256, 219.
22. Selected reviews on silica-supported catalysts: a) Q.-H. Fan, Y.-M. Li, A. S. C. Chan, Chem. Rev. 2002, 102, 3385;
23. b) C. E. Song, S. Lee, Chem. Rev. 2002, 102, 3495;
24. c) D. E. De Vos, M. Dams, B. F. Sets, P. A. Jacobs, Chem. Rev. 2002, 102, 3615;
25. d) J. Y. Ying, C. P. Mehnert, M. S. Wong, Angew. Chem. Int. Ed. 1999, 38, 56.
26. S. Huh, H. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, Angew. Chem. Int. Ed. 2005, 44, 1826.
27. M. Choi, F. Kleitz, D. Liu, H. Y. Lee, W.-S. Ahn, R. Ryoo, J. Am. Chem. Soc. 2005, 127, 1924.
28. a) S. G. Ouellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 32;
29. b) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108;
30. c) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
31. d) S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192;
32. e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894;
33. f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
34. g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370;
35. h) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
36. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874.
37. a) M. T. H. Fonseca, B. List, Angew. Chem. Int. Ed. 2004, 43, 2;
38. b) H. Adolfsson, Angew. Chem. Int. Ed. 2005, 44, 3340;
39. c) W. Wang, H. Li, J. Wang, Org. Lett. 2005, 7, 1637.
40. a) M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149;
41. b) S. A. Selkala, J. Tois, P.M. Pihko, A.M.P. Koskinen, Adv. Synth. Catal. 2002, 344, 941;
42. c) A. Puglisi, M. Benaglia, M. Cinquini, F. Cozzi, G. Celentano, Eur. J. Org. Chem. 2004, 2004, 567;
43. d) C. S. Pecinovsky, G. D. Nicodemus, D. L. Gin, Chem. Mater. 2005, 17, 4889.
44. a) T. Shimada, K. Aoki, Y. Shinoda, T. Nakamura, N. Tokunaga, S. Inagaki, T. Hayashi, J. Am. Chem. Soc. 2003, 125, 4688;
45. b) K. Aoki, T. Shimada, T. Hayashi, Tetrahedron: Asymmetry 2004, 15, 1771.
46. [10b] (equation presented) Without an acid catalyst, significant reaction can be achieved only with silica samples with acidic surfaces, such as FSM-16. By adding 2-5% acid catalyst, a high silane loading could be achieved with various types of silica, even when the reaction was run at room temperature (see Supporting Information for details);
47. b) T. Morita, Y. Okamoto, H. Sakurai, Tetrahedron Lett. 1980, 27, 835.
48. a) S. S. Lee, Y. Han, J. Y. Ying, to be submitted;
49. b) Y. Han, S. S. Lee, J. Y. Ying, Chem. Mater. 2006, 18, 643.
50. a) C. Friedel, J. M. Crafts, Bull. Soc. Chim. Fr. 1877, 27, 530;
51. b) G. A. Olah, R. Krishnamurti, G. K. S. Prakash, Friedel-Crafts Alkylation in Comprehensive Organic Synthesis, Vol. III, 1st edn., (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 293;
52. c) Friedel-Crafts and Related Reactions, (Eds.: G. A. Olah), Wiley, New York, 1965;
53. d) N. Grathergood, W. Zhuang, K. A. Jorgensen, J. Am. Chem. Soc. 2000, 122, 12517.
54. A. Corma, H. Garcia, A. Moussaif, M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058.
55. S. Saito, H. Yamamoto, Acc. Chem. Res. 2004, 37, 570.