Single-site catalysts for ring-opening polymerization: Synthesis of heterotactic poly(lactic acid) from rac-lactide [9]

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11583-11584

  Cheng, Ming ^a   Attygalle, Athula B ^a   Lobkovsky, Emil B ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTIC ACID DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; LETTER; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033572686     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992678o     Document Type: Letter

References (31)

1. Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170.
2. Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997.
3. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39- 48.
4. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39- 48.
5. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39- 48.
6. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39- 48.
7. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39- 48.
8. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39- 48.
9. For some notable exceptions, see: (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072-4073. (b) Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019. (c) Chamberlain, B. M.; Sun, Y. P.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G.; Pink, R.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400-2402. (d) Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Macromol. Chem. Phys. 1996, 197, 2627-2637. (e) Chisholm, M. H.; Eilerts, N. W. Chem. Commun. 1996, 853-854. (f) Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727. (g) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39-48.
10. Chiellini, E.; Solaro, R. Adv. Mater. 1996, 8, 305-313.
11. These polymers are therefore formally poly(lactide)s, but to simplify the stereochemical nomenclature they will be referred to poly(lactic acid)s in this paper.
12. For examples of Al, Mg, Sn, and Y-based alkoxide initiators, see: (a) Dubois, P.; Jacobs, C.; Jérôme, R.; Tessié, P. Macromolecules 1991, 24, 2266-2270. (b) Reference 3e, (c) Kricheldorf, H. R.; Lee, S. R.; Bush, S. Macromolecules 1996, 29, 1375-1381. (d) Stevels, W. M.; Dijkstra, P. J.; Feijen, J. Trends Polym. Sci. 1997, 5, 300-305.
13. For examples of Al, Mg, Sn, and Y-based alkoxide initiators, see: (a) Dubois, P.; Jacobs, C.; Jérôme, R.; Tessié, P. Macromolecules 1991, 24, 2266- 2270. (b) Reference 3e, (c) Kricheldorf, H. R.; Lee, S. R.; Bush, S. Macromolecules 1996, 29, 1375-1381. (d) Stevels, W. M.; Dijkstra, P. J.; Feijen, J. Trends Polym. Sci. 1997, 5, 300-305.
14. For examples of Al, Mg, Sn, and Y-based alkoxide initiators, see: (a) Dubois, P.; Jacobs, C.; Jérôme, R.; Tessié, P. Macromolecules 1991, 24, 2266- 2270. (b) Reference 3e, (c) Kricheldorf, H. R.; Lee, S. R.; Bush, S. Macromolecules 1996, 29, 1375-1381. (d) Stevels, W. M.; Dijkstra, P. J.; Feijen, J. Trends Polym. Sci. 1997, 5, 300-305.
15. For examples of Al, Mg, Sn, and Y-based alkoxide initiators, see: (a) Dubois, P.; Jacobs, C.; Jérôme, R.; Tessié, P. Macromolecules 1991, 24, 2266- 2270. (b) Reference 3e, (c) Kricheldorf, H. R.; Lee, S. R.; Bush, S. Macromolecules 1996, 29, 1375-1381. (d) Stevels, W. M.; Dijkstra, P. J.; Feijen, J. Trends Polym. Sci. 1997, 5, 300-305.
16. Cheng, M.; Ovin, T. M.; Hustad, P. D.; Coates, G. W. Polym. Prepr. 1999, 40 (1), 542-543.
17. For some recent examples of polymerization catalysis with bulky ligands that control stereochemistry by a chain-end control mechanism, see: (a) Small, B. L.; Brookhart, M. Macromolecules 1999, 32, 2120-2130. (b) Resconi, L.; Abis, L.; Franciscono, G. Macromolecules 1992, 25, 6814-6817.
18. For some recent examples of polymerization catalysis with bulky ligands that control stereochemistry by a chain-end control mechanism, see: (a) Small, B. L.; Brookhart, M. Macromolecules 1999, 32, 2120-2130. (b) Resconi, L.; Abis, L.; Franciscono, G. Macromolecules 1992, 25, 6814-6817.
19. Heterotactic macromolecules are a rare type of polymer that have alternating pairs of stereogenic centers in the main chain (i.e. only mr/rm dyads are present). For some recent examples, see: (a) Hirano, T.; Yamaguchi, H.; Kitayama, T.; Hatada, K. Polym. J. 1998, 30, 767-769. (b) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605. (c) Kitayama, T.; Hirano, T.; Hatada, K. Tetrahedron 1997, 53, 15263-15279. (d) Nakahama, S.; Kobayashi, M.; Ishizone, T.; Hirao, A. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1845-1855, (e) Fossum, E.; Matyjaszewski, K. Macromolecules 1995, 28, 1618-1625.
20. Heterotactic macromolecules are a rare type of polymer that have alternating pairs of stereogenic centers in the main chain (i.e. only mr/rm dyads are present). For some recent examples, see: (a) Hirano, T.; Yamaguchi, H.; Kitayama, T.; Hatada, K. Polym. J. 1998, 30, 767-769. (b) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605. (c) Kitayama, T.; Hirano, T.; Hatada, K. Tetrahedron 1997, 53, 15263-15279. (d) Nakahama, S.; Kobayashi, M.; Ishizone, T.; Hirao, A. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1845-1855, (e) Fossum, E.; Matyjaszewski, K. Macromolecules 1995, 28, 1618-1625.
21. Heterotactic macromolecules are a rare type of polymer that have alternating pairs of stereogenic centers in the main chain (i.e. only mr/rm dyads are present). For some recent examples, see: (a) Hirano, T.; Yamaguchi, H.; Kitayama, T.; Hatada, K. Polym. J. 1998, 30, 767-769. (b) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605. (c) Kitayama, T.; Hirano, T.; Hatada, K. Tetrahedron 1997, 53, 15263-15279. (d) Nakahama, S.; Kobayashi, M.; Ishizone, T.; Hirao, A. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1845-1855, (e) Fossum, E.; Matyjaszewski, K. Macromolecules 1995, 28, 1618-1625.
22. Heterotactic macromolecules are a rare type of polymer that have alternating pairs of stereogenic centers in the main chain (i.e. only mr/rm dyads are present). For some recent examples, see: (a) Hirano, T.; Yamaguchi, H.; Kitayama, T.; Hatada, K. Polym. J. 1998, 30, 767-769. (b) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605. (c) Kitayama, T.; Hirano, T.; Hatada, K. Tetrahedron 1997, 53, 15263-15279. (d) Nakahama, S.; Kobayashi, M.; Ishizone, T.; Hirao, A. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1845-1855, (e) Fossum, E.; Matyjaszewski, K. Macromolecules 1995, 28, 1618-1625.
23. Heterotactic macromolecules are a rare type of polymer that have alternating pairs of stereogenic centers in the main chain (i.e. only mr/rm dyads are present). For some recent examples, see: (a) Hirano, T.; Yamaguchi, H.; Kitayama, T.; Hatada, K. Polym. J. 1998, 30, 767-769. (b) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605. (c) Kitayama, T.; Hirano, T.; Hatada, K. Tetrahedron 1997, 53, 15263-15279. (d) Nakahama, S.; Kobayashi, M.; Ishizone, T.; Hirao, A. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1845-1855, (e) Fossum, E.; Matyjaszewski, K. Macromolecules 1995, 28, 1618-1625.
24. tBu polymerizes rac-lactide to PLA that is enriched in heterotactic sequences: Kasperczyk, J. E. Macromolecules 1995, 28, 3937-3939.
25. (a) Thakur, K. A. M.; Kean, R. T.; Hall, E. S.; Kolstad, J. J.; Lindgren, T. A.; Doscotch, M. A.; Siepmann, J. I.; Munson, E. J. Macromolecules 1997, 30, 2422-2428.
26. (b) Thakur, K. A. M.; Kean, R. T., Hall, E. S.; Kolstad, J. J.; Munson, E. J. Macromolecules 1998, 31, 1487-1494.
27. (c) Wisniewski, M.; Le Borgne, A.; Spassky, N. Macromol. Chem. Phys. 1997, 198, 1227-1238.
28. (d) Coudane, J.; Ustariz-Peyret, C.; Schwach, G.; Vert, M. J. Polym. Sci., Polym. Chem. Ed. 1997, 35, 1651-1658.
29. Crystal data of 2: orthorhombic, Pbca, colorless; a = 21.4727(4) Å, b = 19.5105(3) Å, c = 33.3509(3) Å: V = 13972.1(4); Z = 8; R = 0.0540; GOF = 1.033.
30. 2/2.
31. Thakur, K. A. M.; Kean, R. T.; Zell, M. T.; Padden, B. E.; Munson, E. J. Chem. Commun. 1998, 1913-1914.