Facile Synthesis of Polymer-Supported Cinchona Alkaloid Catalysts for Asymmetric Michael Reaction

Polymer Journal

Volumn 36, Issue 3, 2004, Pages 190-197

  Onimura, Kenjiro ^a   Matsuzaki, Kouhei ^a   Lee, Yong Kyung ^a   Tsutsumi, Hiromori ^a   Oishi, Tsutomu ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

2 Methacryloyloxyethyl Isocyanate; Asymmetric Catalyst; Asymmetric Michael Reaction; Cinchona Alkaloid; Optically Active Polymer; Polymer Supported Catalyst

Indexed keywords

CATALYSTS; CHEMICAL BONDS; FREE RADICAL POLYMERIZATION; MOLECULAR ORIENTATION; MOLECULAR WEIGHT; MONOMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

2-METHACRYLOYLOXYETHYL ISOCYANATE; ASYMMETRIC CATALYST; ASYMMETRIC MICHAEL REACTION; CINCHONA ALKALOID; OPTICALLY ACTIVE POLYMER; POLYMER-SUPPORTED CATALYST;

REACTION KINETICS;

EID: 2342619570     PISSN: 00323896     EISSN: None     Source Type: Journal    
DOI: 10.1295/polymj.36.190     Document Type: Article

References (28)

1. D. E. De Vos, I. F. J. Vankelecom, and P. A. Jacobs, Ed., in "Chiral Catalyst Immobilization and Recycling," Wiley-VCH, Weinheim, Germany, 2000.
2. For a recent review on the use of polymeric catalysts see: (a) Q.-H. Fan, Y.-M. Li, and A. S. C. Chan, Chem. Rev., 102, 3385 (2002). (b) B. Clapham, T. S. Reger, and K. Janda, Tetrahedron, 57, 4637 (2001).
3. For a recent review on the use of polymeric catalysts see: (a) Q.-H. Fan, Y.-M. Li, and A. S. C. Chan, Chem. Rev., 102, 3385 (2002). (b) B. Clapham, T. S. Reger, and K. Janda, Tetrahedron, 57, 4637 (2001).
4. Review on the use of Cinchona alkaloids as organic catalysts: K. Kacprzak and J. Gawronski, Synthesis, 2001, 961.
5. (a) N. Kobayashi and K. Iwai, J. Am. Chem. Soc., 100, 7071 (1978).
6. (b) N. Kobayashi and K. Iwai, J. Polym. Sci., Polym. Chem. Ed., 18, 223 (1980).
7. (c) N. Kobayashi and K. Iwai, J. Polym. Sci., Polym. Chem. Ed., 18, 923 (1980).
8. (d) N. Kobayashi and K. Iwai, Macromolecules, 13, 31 (1980).
9. (e) N. Kobayashi and K. Iwai, J. Polym. Sci., Polym. Lett. Ed., 18, 417 (1980).
10. (f) N. Kobayashi and K. Iwai, Tetrahedron Lett., 21, 2167 (1980).
11. (g) N. Kobayashi and K. Iwai, J. Polym. Sci., Polym. Lett. Ed., 20, 85 (1982).
12. H. Danda, K. Chino, and S. Wake, Chem. Lett., 1991, 731.
13. P. Hodge, E. Khoshdel, and J. Waterhouse, J. Chem. Soc., Perkin Trans. I, 1983, 2205.
14. M. Inagaki, J. Hiratake, Y. Yamamoto, and J. Oda, Bull. Chem. Soc. Jpn., 60, 4121 (1987).
15. B. B. Lohray, E. Nandanan, and V. Bhushan, Tetrahedron Lett., 35, 6559 (1994).
16. L. Canali, C. E. Song, and D. C. Sherrington, Tetrahedron: Asymmetry, 9, 1029 (1998).
17. R. Alvarez, M.-A. Hourdin, C. Cavé, J. d'Angelo, and P. Chaminade, Tetrahedron Lett., 40, 7091 (1999).
18. V. Athawale and N. Manjrekar, Tetrahedron Lett., 42, 4541 (2001).
19. (a) Y.-K. Lee, Y. Nakashima, K. Onimura, H. Tsutsumi, and T. Oishi, Macromolecules, 36, 4735 (2003).
20. (b) Y.-K. Lee, N. Hisamitsu, K. Onimura, H. Tsutsumi, and T. Oishi, Polym. J., 34, 9 (2002).
21. (a) Y.-K. Lee, K. Onimura, H. Tsutsumi, and T. Oishi, Polym. J., 33, 411 (2001).
22. (b) Y.-K. Lee, K. Onimura, H. Tsutsumi, and T. Oishi, Polym. J., 32, 1007 (2000).
23. (c) Y.-K. Lee, K. Onimura, H. Tsutsumi, and T. Oishi, J. Polym. Sci., Part A: Polym. Chem., 38, 4315 (2000).
24. H. O. House and C. B. Hudson, J. Org. Chem., 35, 647 (1970).
25. Y.-K. Lee, K. Yamashita, M. Eto, K. Onimura, H. Tsutsumi, and T. Oishi, Polymer, 43, 7539 (2002).
26. (a) M. Nakajima, Y. Yamaguchi, and S. Hashimoto, Chem. Commun., 2001, 1596.
27. (b) M. Nakajima, S. Yamamoto, Y. Yamaguchi, S. Nakamura, and S. Hashimoto, Tetrahedron, 59, 7307 (2003).
28. A. Sera, K. Takagi, H. Katayama, and H. Yamada, J. Org. Chem., 53, 1157 (1998).