Effects of primary and secondary surface groups in enantioselective catalysis using nanoporous materials with chiral walls

Journal of the American Chemical Society

Volumn 132, Issue 18, 2010, Pages 6558-6565

  Kuschel, Andreas ^a   Polarz, Sebastian ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL-ENE REACTIONS; CATALYTIC ACTIVITY; CATALYTIC CENTER; CHIRAL BUILDING BLOCKS; CHIRAL GROUPS; CHIRAL SURFACE; COOPERATIVE EFFECTS; ENANTIOSELECTIVE CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; LEWIS ACID; MESOPOROUS ORGANOSILICA MATERIALS; MODEL SYSTEM; MOLECULAR CATALYSTS; NANOPOROUS MATERIALS; ORDERED MESOPOROUS ORGANOSILICA; PORE WALL; REFERENCE CATALYST; SILANOL GROUPS; SURFACE GROUPS;

CATALYSTS; MATERIALS; MESOPOROUS MATERIALS; SYNTHESIS (CHEMICAL); WALLS (STRUCTURAL PARTITIONS);

SURFACES;

1 (3,5 BIS TRI ISO PROPOXYSILYLPHENYL) ETHANOL; 1 (3,5 BIS TRI ISO PROPOXYSILYLPHENYL) ETHANONE; 1 (3,5 BIS TRI ISOPROPOXYSILYPHENYL) ETHANOL; 1,3 BIS TRI ISO PROPOXYSILYL 5 BROMOBENZENE; BROMOBENZENE; LEWIS ACID; SILANOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; IMMOBILIZATION; INFRARED SPECTROSCOPY; NANOPORE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE MEASUREMENT;

ALUMINUM; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; NANOSTRUCTURES; POROSITY; SILICON DIOXIDE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SURFACE PROPERTIES; TEMPERATURE;

EID: 77952015659     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1017706     Document Type: Article

References (59)

1. Kolb, H. C., Vannieuwenhze, M. S., and Sharpless, K. B. Chem. Rev. 1994, 94, 2483
2. Grubbs, R. H. and Chang, S. Tetrahedron 1998, 54, 4413
3. Stephenson, G. R. E. Advanced Asymmetric Synthesis; Chapman & Hall: London, 1996.
4. Procter, G. Stereoselectivity in Organic Synthesis; Oxford University Press: Oxford, U.K., 1998.
5. Cox, G. B. Preparative Enantioselective Chromatography; Blackwell Publishing: Oxford, U.K., 2005.
6. Dalko, P. I. and Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726
7. Dalko, P. I. and Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138
8. Corma, A. and Garcia, H. Adv. Synth. Catal. 2006, 348, 1391
9. Fraile, J. M., Garcia, J. I., Herrerias, C. I., Mayoral, J. A., and Pires, E. Chem. Soc. Rev. 2009, 38, 695
10. Li, C., Zhang, H. D., Jiang, D. M., and Yang, Q. H. Chem. Commun. 2007, 547
11. Taguchi, A. and Schueth, F. Microporous Mesoporous Mater. 2005, 77, 1
12. Climent, M. J., Corma, A., Iborra, S., Miquel, S., Primo, J., and Rey, F. J. Catal. 1999, 183, 76
13. Polarz, S. and Smarsly, B. J. Nanosci. Nanotechnol. 2003, 2, 581
14. Kresge, C. T., Leonowicz, M., Roth, W. J., Vartuli, J. C., and Beck, J. S. Nature. 1992, 359, 710
15. Yang, P., Zhao, D., Margolese, D. I., Chmelka, B. F., and Stucky, G. D. Nature 1998, 396, 152
16. Hoffmann, F., Cornelius, M., Morell, J., and Froeba, M. Angew. Chem., Int. Ed. 2006, 45, 3216
17. Luechinger, M., Kienhofer, A., and Pirngruber, G. D. Chem. Mater. 2006, 18, 1330
18. Zhang, Q. M., Ariga, K., Okabe, A., and Aida, T. J. Am. Chem. Soc. 2004, 126, 988
19. Asefa, T., MacLachan, M. J., Coombs, N., and Ozin, G. A. Nature. 1999, 402, 867
20. Inagaki, S., Guan, S., Fukushima, Y., Ohsuna, T., and Terasaki, O. J. Am. Chem. Soc. 1999, 121, 9611
21. Melde, B. J., Holland, B. T., Blanford, C. F., and Stein, A. Chem. Mater. 1999, 11, 3302
22. MacLachlan, M. J., Asefa, T., and Ozin, G. A. Chem. - Eur. J. 2000, 6, 2507
23. Hatton, B., Landskron, K., Whitnall, W., Perovic, D., and Ozin, G. A. Acc. Chem. Res. 2005, 38, 305
24. Baleizao, C., Gigante, B., Das, D., Alvaro, M., Garcia, H., and Corma, A. J. Catal. 2004, 223, 106
25. Baleizao, C., Gigante, B., Garcia, H., and Corma, A. J. Catal. 2003, 215, 199
26. Baleizao, C., Gigante, B., Das, D., Alvaro, M., Garcia, H., and Corma, A. Chem. Commun. 2003, 1860
27. Zhang, H. D., Zhang, Y. M., and Li, C. J. Catal. 2006, 238, 369
28. Zhang, H. and Li, C. Tetrahedron 2006, 62, 6640
29. Jiang, D. M., Gao, J. S., Yang, Q. H., Yang, J., and Li, C. Chem. Mater. 2006, 18, 6012
30. Polarz, S. and Kuschel, A. Adv. Mater. 2006, 18, 1206
31. Ide, A., Voss, R., Scholz, G., Ozin, G. A., Antonietti, A., and Thomas, A. Chem. Mater. 2007, 19, 2649
32. Kuschel, A., Sievers, H., and Polarz, S. Angew. Chem., Int. Ed. 2008, 47, 9513
33. Morell, J., Chatterjee, S., Klar, P. J., Mauder, D., Shenderovich, I., Hoffmann, F., and Froeba, M. Chem. - Eur. J. 2008, 14, 5935
34. MacQuarrie, S., Thompson, M. P., Blanc, A., Mosey, N. J., Lemieux, R. P., and Crudden, C. M. J. Am. Chem. Soc. 2008, 130, 14099
35. Yang, Q. H., Han, D. F., Yang, H. Q., and Li, C. Chem. - Asian J. 2008, 3, 1214
36. Li, C. Catal. Rev. - Sci. Eng. 2004, 46, 419
37. Heitbaum, M., Glorius, F., and Escher, I. Angew. Chem., Int. Ed. 2006, 45, 4732
38. Kuschel, A., Drescher, M., Kuschel, T., and Polarz, S. Chem. Mater. 2010, 22, 1472
39. Seo, J. S., Whang, D., Lee, H., Jun, S. I., Oh, J., Jeon, Y. J., and Kim, K. Nature 2000, 404, 982
40. Lin, W. B. J. Solid State Chem. 2005, 178, 2486
41. Wu, C. D. and Lin, W. B. Angew. Chem., Int. Ed. 2005, 44, 1958
42. Clarke, M. L. and France, M. B. Tetrahedron 2008, 64, 9003
43. Kuschel, A. and Polarz, S. Adv. Funct. Mater. 2008, 18, 1272
44. Polarz, S. and Kuschel, A. Chem. - Eur. J. 2008, 14, 9816
45. Kuschel, A., Luka, M., Wessig, M., Drescher, M., Fonin, M., Kiliani, G., and Polarz, S. Adv. Funct. Mater. 2010, 20, 1133
46. Disimone, B., Savoia, D., Tagliavini, E., and Umanironchi, A. Tetrahedron: Asymmetry 1995, 6, 301
47. Parker, D. Chem. Rev. 1991, 91, 1441
48. Sullivan, G. A., Dale, J. A., and Mosher, H. S. J. Org. Chem. 1973, 38, 2143
49. Zhao, D., Feng, J., Huo, Q., Melosh, N., Fredrickson, G. H., Chmelka, B. F., and Stucky, G. D. Science 1998, 279, 548
50. Attard, G. S., Glyde, J. G., and Goeltner, C. G. Nature 1995, 378, 366
51. Attard, G. S., Goeltner, C. G., Corker, J. M., Henke, S., and Templer, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1315
52. Polarz, S. and Antonietti, M. Chem. Commun. 2002, 2593
53. Gregg, S. J. and Sing, K. S. W. Adsorption, Surface Area and Porosity, 4 th ed.; Academic Press: London, 1982; Vol. 2.
54. Rouqerol, J., Avnir, D., Fairbridge, C. W., Everett, D. H., Haynes, J. H., Pernicone, N., Ramsay, J. D., Sing, K. S. W., and Unger, K. K. Pure Appl. Chem. 1994, 66, 1739
55. Brunauer, S., Emmet, P. H., and Teller, E. J. Am. Chem. Soc. 1938, 60, 309
56. Barret, E. P., Joyner, L. G., and Halenda, P. H. J. Am. Chem. Soc. 1951, 73, 373
57. Yoshina-Ishii, C., Asefa, T., Coombs, N., MacLachlan, M. J., and Ozin, G. A. Chem. Commun. 1999, 2539
58. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008
59. Polarz, S., Smarsly, B., Bronstein, L., and Antonietti, M. Angew. Chem., Int. Edit. 2001, 40, 4417