A dendrimer-supported heterobimetallic asymmetric catalyst

Tetrahedron Asymmetry

Volumn 13, Issue 19, 2002, Pages 2083-2087

  Arai, Takayoshi ^a   Sekiguti, Tetuya ^a   Iizuka, Yoshimasa ^a   Takizawa, Shinobu ^a   Sakamoto, Shigeru ^b   Yamaguchi, Kentaro ^b   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; DENDRIMER; LIGAND; MALONIC ACID DERIVATIVE; METAL DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; MASS SPECTROMETRY; MOLECULAR DYNAMICS; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0037020481     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00573-6     Document Type: Article

References (38)

1. . For a recent review: Grayson S.M., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867.
2. For recent reviews, see: (a) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; P. van Leeuwen, W. N. M. Angew. Chem., Int. Ed. 2001, 40, 1828-1849; (b) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991-3023; (c) Kreiter, R.; Kleji, A. W.; Klein Gebbink, R. J. M.; van Koten, G. In Topics in Current Chemistry; Vögtle, F.; Schalley, C. A., Eds. Metal Coordination, Self Assembly, Catalysis. Springer: Berlin, 2001; Vol. 217: Dendrimers IV, pp. 163-199.
3. For recent reviews, see: (a) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; P. van Leeuwen, W. N. M. Angew. Chem., Int. Ed. 2001, 40, 1828-1849; (b) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991-3023; (c) Kreiter, R.; Kleji, A. W.; Klein Gebbink, R. J. M.; van Koten, G. In Topics in Current Chemistry; Vögtle, F.; Schalley, C. A., Eds. Metal Coordination, Self Assembly, Catalysis. Springer: Berlin, 2001; Vol. 217: Dendrimers IV, pp. 163-199.
4. For recent reviews, see: (a) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; P. van Leeuwen, W. N. M. Angew. Chem., Int. Ed. 2001, 40, 1828-1849; (b) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991-3023; (c) Kreiter, R.; Kleji, A. W.; Klein Gebbink, R. J. M.; van Koten, G. In Topics in Current Chemistry; Vögtle, F.; Schalley, C. A., Eds. Metal Coordination, Self Assembly, Catalysis. Springer: Berlin, 2001; Vol. 217: Dendrimers IV, pp. 163-199.
5. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
6. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
7. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
8. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
9. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
10. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
11. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
12. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
13. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
14. For representative examples of positive effects of dendrimer-supported catalysis, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529; (b) Francavilla, C.; Bright, F. V.; Detty, M. R. Org. Lett. 1999, 1, 1043-1046; (c) Yamago, S.; Furukawa, M.; Azuma, A,; Yoshida, J. Tetrahedron Lett. 1998, 39, 3783-3786; (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Eur. J. 1999, 5, 3495-3500; (e) Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329-333; (f) Piotti, M. E.; Rivera, F., Jr.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472; (g) Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126; (h) Maraval, V.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P. Organometallics 2000, 19, 4025-4029; (i) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789-790; (j) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361-362.
15. Breinbauer R., Jacobsen E.N. Angew. Chem., Int. Ed. Engl. 39:2000;3604-3607.
16. Sasai H., Arai T., Satow Y., Houk K.N., Shibasaki M. J. Am. Chem. Soc. 117:1995;6194-6198.
17. Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
18. Recent progress with re-usable heterobimetallic multifunctional asymmetric catalysts, see: (a) Arai, T.; Hu, Q.-S.; Zheng, X.-F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261-4263; (b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506-6507; (c) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473-8478; (d) Jayaprakash, D.; Sasai, H. Tetrahedron: Asymmetry 2001, 12, 2589-2595.
19. Recent progress with re-usable heterobimetallic multifunctional asymmetric catalysts, see: (a) Arai, T.; Hu, Q.-S.; Zheng, X.-F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261-4263; (b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506-6507; (c) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473-8478; (d) Jayaprakash, D.; Sasai, H. Tetrahedron: Asymmetry 2001, 12, 2589-2595.
20. Recent progress with re-usable heterobimetallic multifunctional asymmetric catalysts, see: (a) Arai, T.; Hu, Q.-S.; Zheng, X.-F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261-4263; (b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506-6507; (c) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473-8478; (d) Jayaprakash, D.; Sasai, H. Tetrahedron: Asymmetry 2001, 12, 2589-2595.
21. Recent progress with re-usable heterobimetallic multifunctional asymmetric catalysts, see: (a) Arai, T.; Hu, Q.-S.; Zheng, X.-F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261-4263; (b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506-6507; (c) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473-8478; (d) Jayaprakash, D.; Sasai, H. Tetrahedron: Asymmetry 2001, 12, 2589-2595.
22. Molecular dynamics simulations using polymer specific consistent forcefield (PCFF) were performed on Cerius 2 (Accelrys Inc.).
23. Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137-3140.
24. Freeman A.W., Chrisstoffels L.A.J., Fréchet J.M.J. J. Org. Chem. 65:2000;7612-7617.
25. Elmorsy S.S., Pelter A., Smith K. Tetrahedron Lett. 32:1991;4175-4176.
26. 3); Mw on GPC analysis: 2600-2800.
27. Sakamoto S., Fujita M., Kim K., Yamaguchi K. Tetrahedron. 56:2000;955-964.
28. 3); Mw on GPC analysis: 5500-5700.
29. Tsunoda T., Nagaku M., Nagino C., Kawamura Y., Ozaki F., Hioki H., Ito S. Tetrahedron Lett. 36:1995;2531-2534.
30. Reppy M.A., Gray D.H., Pindzola B.A., Smithers J.L., Gin D.L. J. Am. Chem. Soc. 123:2001;363-371.
31. 3 and n-BuLi. The polymer supported ALB gave 13 in 27% yield with 0% ee after 72 h.
32. Under high dilution conditions (0.03 M G1 dendritic ALB), the Michael adduct was obtained with 94% ee, which strongly suggests that the ALB complex forms on a single independent dendrimer molecule.
33. The ALB catalyst derived from the peripheral dendron unit i gave 13 in 72% yield with 97% ee after 48 h.
34. The recovered 8 was able to re-use as a ligand giving the Michael adduct in 63% yield with 91% ee.
35. In the 4th use, 13 was obtained in 57% yield with 79% ee.
36. Arai T., Yamada Y.M.A., Yamamoto N., Sasai H., Shibasaki M. Chem. Eur. J. 2:1996;1368-1372.
37. Equivalency to the single catalytic site.
38. 2, acetone/hexane=1/10) gave 13. The enantiomeric purity of the product was determined by chiral HPLC analysis (Daicel CHIRALPAK AS, i-PrOH/hexane=1/4, 1.0 mL/min, 254 nm).