Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides

Journal of the American Chemical Society

Volumn 121, Issue 17, 1999, Pages 4147-4154

  Annis, D Allen ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; POLYSTYRENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; FILTRATION; KINETICS; REACTION ANALYSIS; REACTION TIME;

EID: 0033526360     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984410n     Document Type: Article

References (54)

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11. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
12. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
13. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126-3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
14. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
15. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
16. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
17. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
18. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
19. For recent examples and related efforts, see: (a) Han, H.; Janda, K. D Tetrahedron Lett. 1997, 38, 1527-1530. (b) Wan, K. T.; Davis, M. Nature 1994, 570, 449-450. (c) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Asym. 1996, 7, 2805-2808. (d) Altava, B.; Burguete, M. I.; Escudar, B.; Luis, S. V.; Salvador, R. V. J. Org. Chem. 1997, 62, 3126- 3134. (e) Nanadanan, E.; Sudalai, A.; Ravindranathanan, T. Tetrahedron Lett. 1997, 38, 2577-2580. (f) Huang, W. S.; Hu, Q. S.; Zheng, X. F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313-4314. (g) Kamahori, K.; Ito, K.; Itsuno, S. J. Org. Chem. 1996, 61, 8321-8324. (h) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633. (i) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930. (j) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
20. It should be noted, however, that these problems are at least partly avoided in the recently developed methods for immobilizing chiral catalysts noncovalently within membranes or polymer matrixes. See: (a) Vancelecom, I. F. J.; Tas, D.; Parton, R. F.; Van de Vyver, V.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1346-1348. (b) Janssen, K. B. M.; Laquiere, I.; Dehaen, W.; Parton, R. F.; Vankelecom, I. F. J.; Jacobs, P. A. Tetrahedron Asym. 1997, 8, 3481-3487.
21. It should be noted, however, that these problems are at least partly avoided in the recently developed methods for immobilizing chiral catalysts noncovalently within membranes or polymer matrixes. See: (a) Vancelecom, I. F. J.; Tas, D.; Parton, R. F.; Van de Vyver, V.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1346-1348. (b) Janssen, K. B. M.; Laquiere, I.; Dehaen, W.; Parton, R. F.; Vankelecom, I. F. J.; Jacobs, P. A. Tetrahedron Asym. 1997, 8, 3481-3487.
22. (a) Water: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. (b) Trimethylsilyl azide: Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Schaus, S. E.; Larrow, J. F.; Jacobsen., E. N. J. Org. Chem. 1997, 62, 4197-4199. Larrow, J. F.; Schaus, S. E.; Jacobsen., E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421. (c) Carboxylic acids: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776. (d) Thiols: Wu, M.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252-5254.
23. (a) Water: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. (b) Trimethylsilyl azide: Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Schaus, S. E.; Larrow, J. F.; Jacobsen., E. N. J. Org. Chem. 1997, 62, 4197-4199. Larrow, J. F.; Schaus, S. E.; Jacobsen., E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421. (c) Carboxylic acids: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776. (d) Thiols: Wu, M.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252-5254.
24. (a) Water: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. (b) Trimethylsilyl azide: Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Schaus, S. E.; Larrow, J. F.; Jacobsen., E. N. J. Org. Chem. 1997, 62, 4197-4199. Larrow, J. F.; Schaus, S. E.; Jacobsen., E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421. (c) Carboxylic acids: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776. (d) Thiols: Wu, M.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252-5254.
25. (a) Water: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. (b) Trimethylsilyl azide: Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Schaus, S. E.; Larrow, J. F.; Jacobsen., E. N. J. Org. Chem. 1997, 62, 4197-4199. Larrow, J. F.; Schaus, S. E.; Jacobsen., E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421. (c) Carboxylic acids: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776. (d) Thiols: Wu, M.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252-5254.
26. (a) Water: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. (b) Trimethylsilyl azide: Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Schaus, S. E.; Larrow, J. F.; Jacobsen., E. N. J. Org. Chem. 1997, 62, 4197-4199. Larrow, J. F.; Schaus, S. E.; Jacobsen., E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421. (c) Carboxylic acids: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776. (d) Thiols: Wu, M.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252-5254.
27. (a) Water: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. (b) Trimethylsilyl azide: Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Schaus, S. E.; Larrow, J. F.; Jacobsen., E. N. J. Org. Chem. 1997, 62, 4197-4199. Larrow, J. F.; Schaus, S. E.; Jacobsen., E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421. (c) Carboxylic acids: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776. (d) Thiols: Wu, M.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 5252-5254.
28. Synthesis of 2: Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
29. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
30. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
31. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
32. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
33. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
34. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
35. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
36. Several previous efforts to immobilize (salen)Mn-based epoxidation catalysts have been described. However, the tendency of (salen)Mn complexes to undergo decomposition under conditions of catalysis limits the attractiveness of immobilization strategies for these particular systems. See ref 7a and: (a) Minutolo, F.; Pini, D.; Salvadori, P. Tetrahedron Lett. 1996, 37, 3375-3378. (b) De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymm. 1995, 6, 2105-2108. (c) Das, B. C.; Iqubal, J. Tetrahedron Lett. 1997, 38, 2903-2906. (d) Chang, S. Ph.D. Thesis, Harvard University, 1996. (e) Ogunwumi, S. G.; Bein, T. J. Chem. Soc., Chem. Commun. 1997, 901. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 22, 7581-7587. (g) Canali, L.; Cowan, E.; Gibson, C. L.; Sherrington, D. C.; Deleuze, H. J. Chem. Soc., Chem. Commun. 1998, 2561-2562. (h) Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293-2302.
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