Functionalized Cross-Linked Copolymers: A "C2-Symmetric" Solid-Phase Catalyst for Enantioselective Reactions

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 510-512

  Halm, Chris ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Asymmetric catalysis; Cross linking; Lewis acids; Polymers; Sulfonamides

Indexed keywords

EID: 0032473520     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<510::aid-anie510>3.0.co;2-9     Document Type: Article

References (30)

1. R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149- 2154.
2. Reviews on solid-phase organic reactions: a) P. Hermkens, H. Ottenheijm, D. Rees, Tetrahedron 1997, 53, 5643-5678; b) ibid. 1996, 52, 4527-4554.
3. Reviews on solid-phase organic reactions: a) P. Hermkens, H. Ottenheijm, D. Rees, Tetrahedron 1997, 53, 5643-5678; b) ibid. 1996, 52, 4527-4554.
4. a) J. Parlow, Tetrahedron Lett. 1995, 36, 1395-1396;
5. b) P. Wipf, S. Venkatraman, ibid. 1996, 37, 4659-4662;
6. c) A. Guyot, P. Hodge, D. Sherrington, H. Widdecke, Reactive Polymers, 1991, 16, 233-259.
7. a) S. Itsuno, K. Kamahori, K. Watanabe, T. Koizumi, K. Ito, Tetrahedron: Asymmetry 1994, 5, 523-526;
8. b) M. Zupan, D. Dolenc, Tetrahedron 1991, 47, 5025-5028;
9. c) M. Zupan, N. Segatin, Synth. Commun. 1991, 21, 597-609;
10. d) review; S. Schlick, E. Bortel, K. Dyrek, Acta Polym. 1996, 47, 1-15.
11. J. S. Fruechtel, G. Jung, Angew. Chem. 1996, 108, 19-46;
12. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42.
13. a) H. Han, M. Wolfe, S. Brenner, K. Janda, Proc. Natl. Acad. Sci. USA 1995, 92, 6419-6423;
14. b) R. Quarrell, T. Claridge, G. Weaver, G. Lowe, Molecular Diversity 1996, 1, 223-232;
15. c) B. Zhao, G. Panigrahi, P. Sadowski, J. Krepinsky, Tetrahedron Lett. 1996, 37, 3093-3096;
16. d) J. W. Labadie, T. L. Deegan, O. W. Gooding, K. Heisler, W. S. Newcomb, J. A. Porco, Jr., T. H. Tran, P. van Eikeren, Polym. Mater. Sci. Eng. 1996, 75, 389-390.
17. a) S. Itsuno, Y. Sakurai, K. Ito, T. Maruyama, S. Nakahama, J. Frechet, J. Org. Chem. 1990, 55, 304-310;
18. b) G. Liu, J. Ellman, ibid. 1995, 60, 7712-7713.
19. a) B. De, B. Lohray, S. Sivaram, P. Dhal, Tetrahedron: Asymmetry 1995, 9, 2105-2108;
20. b) F. Minutolo, D. Pini, P. Salvadori, Tetrahedron Lett. 1996, 17, 3375-3378.
21. J. Whitesell, Chem. Rev. 1989, 89, 1581-1590.
22. a) M. Yoshioka, T. Kawakita, M. Ohno, Tetrahedron Lett. 1989, 13, 1657-1660;
23. b) H. Takahashi, ibid. 1989, 50, 7095-7098.
24. For chiral resolution, see T. Whitney, J. Org. Chem. 1980, 45, 4214-4216.
25. H. Kamogawa, A. Kanzawa, M. Kadoya, T. Naito, M. Nanasawa, Bull. Chem. Soc. Jpn. 1983, 56, 762-765.
26. G. Odian, Principles of Polymerization, Wiley, New York, 1981.
27. a) H. Takahashi, M. Yoshioka, M. Ohno, S. Kobayashi, Tetrahedron Lett. 1992, 18, 2575-2578;
28. b) Lewis acid catalyzed cyclopropanations: A. Charette, C. Brochu, J. Am. Chem. Soc. 1995, 117, 11367-11368.
29. Enantioselectivities can be increased by replacing the phenyl with a nitrophenyl group in 6, see S. Denmark, B. Christenson, S. O'Connor, Tetrahedron Lett. 1995, 36, 2219-2222.
30. a) S. Denmark, B. Christenson, D. Coe, S. O'Connor, Tetrahedron Lett. 1995, 36, 2215-2218.