"Catalyst analogue": A concept for constructing multicomponent asymmetric catalysts (MAC) by using a polymer support

Angewandte Chemie - International Edition

Volumn 42, Issue 19, 2003, Pages 2144-2147

  Arai, Takayoshi ^a   Sekiguti, Tetuya ^a   Otsuki, Kazuhiro ^a   Takizawa, Shinobu ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Immobilization; Polymerization; Synthetic methods

Indexed keywords

COPOLYMERIZATION; OLEFINS; ORGANIC POLYMERS;

MULTICOMPONENT ASYMMETRIC CATALYSTS (MAC);

ENZYMES;

ALKENE DERIVATIVE; LIGAND; METAL; METHACRYLIC ACID METHYL ESTER; MONOMER; NAPHTHOL DERIVATIVE; POLYMER;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CROSS LINKING; MOLECULAR STABILITY; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038245255     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250536     Document Type: Article

References (36)

1. Representative examples of MACs: a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517-519; Angew. Chem. Int. Ed. 1999, 38, 495-497;
2. Representative examples of MACs: a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517-519; Angew. Chem. Int. Ed. 1999, 38, 495-497;
3. b) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8180-8186;
4. c) H. Furuno, T. Hanamoto, Y. Sugimoto, J. Inanaga, Org. Lett. 2000, 2, 49-52;
5. d) S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083-4084. See also reference [2].
6. For recent reviews, see: a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236-1256;
7. For recent reviews, see a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236-1256;
8. b) G. J. Rowlands, Tetrahedron 2001, 57, 1865-1882;
9. c) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2209.
10. a) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103-105; Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106;
11. a) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103-105; Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106;
12. b) T. Arai, Y. M. A. Yamada, N. Yamamoto, H. Sasai, M. Shibasaki, Chem. Eur. J. 1996, 2, 1368-1372;
13. c) T. Arai, H. Sasai, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 441-442.
14. D. J. Bayston, J. L. Fraser, M. R. Ashton, A. D. Baxter, M. E. C. Polywka, E. Moses, J. Org. Chem. 1998, 63, 3137-3140.
15. The monomer 1b was stable under neutral anhydrous conditions. The diasteroselectivity on 1b was about 1:1.
16. The amount of AIBN and the crosslinker is based on the total amount of 1b and MMA.
17. The polymer-supported ALB generated from the polymer prepared in the ratio of 1b:MMA = 1:1 and 3:MMA = 1:1 gave the Michael adduct 12 with 48% ee and 2% ee, respectively.
18. w = 24000, PDI = 1.81).
19. The polymer-supported ALB prepared by use of 30 mol% and/or 90 mol% of crosslinker gave 12 in 32% yield with 39% ee and 32% yield with 36% ee, respectively.
20. MIPs have been produced to order for the construction of chemo- and/or stereoselective receptors, sensors, columns, and/or artificial enzymes by using multisite recognition. In the application of MIPs to asymmetric metal catalysis, the molecular imprinting process is carried out using a chiral template of a transition state analogue, which is then removed for constructing a chiral cavity after the polymerization. Thus, the catalytic activities and selectivities are highly dependent on the efficiency of imprinting and the rigidity of the cavity. The requirement of a high loading of crosslinker for keeping the cavity rigid causes a serious decline in the activity of the catalyst.
21. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
22. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
23. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
24. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
25. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
26. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
27. For recent reviews on MIP, see: a) Molecularly Imprinted Polymers (Ed.: B. Sellergren), Elsevier, Amsterdam, 2000; b) K. Haupt, K. Mosbach, Chem. Rev. 2000, 100, 2495-2504; c) G. Wulff, Chem. Rev. 2002, 102, 1-27; Representative examples of MIPs of asymmetric metal catalysts: d) J. H. Koh, A. O. Larsen, P. S. White, M. R. Gagné, Organometallics 2002, 21, 7-9; e) K. Polborn, K. Severin, Eur. Jr. Inorg. Chem. 2000, 1687-1692; f) M. R. Gagné, J. J. Becker, N. M. Brunkan, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2000, 41, 404; g) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
28. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
29. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
30. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
31. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
32. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
33. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
34. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
35. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
36. Recent progress in reusable multicomponent asymmetric catalysts: a) T. Arai, Q.-S. Hu, X.-E Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261-4263; b) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507; c) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478; d) D. Jayaprakash, H. Sasai, Tetrahedron: Asymmetry 2001, 12, 2589-2595; e) T. Arai, T. Sekiguti, Y. Iizuka, S. Takizawa, S. Sakamoto, K. Yamaguchi, H. Sasai, Tetrahedron: Asymmetry 2002, 13, 2083-2087; f) T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369-375; g) H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501; h) G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389-392; i) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.