JandaJels™

Chemfiles Volume 5 Article 11

JandaJels are designed to create a “solvent-like organic microenvironment to catalyze organic reactions”.1 The flexible tetrahydrofuran-like cross-linker gives the JandaJels increased swelling and solvation characteristics as compared to polystyrene resins cross-linked with divinylbenzene.2,3 The increased swelling results in better site accessibility as compared to highly crosslinked polymers.4 JandaJels have been used for solid-supported organic synthesis (SPOS)5–8 as well as polymer-bound reagents in a wide variety of synthetic transformations,9–11 catalysis,12,13 chiral catalysis,14–17 and in small library synthesis.18–23


Synthesis of a Phthalimide Library18


Synthesis of a Di-, Tri-, and Tetra-substituted Urea Library19


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Materials

     

References

  1. Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329.
  2. Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579.
  3. Gambs, C.; Dickerson, T.; Mahajen, S.; Pasternack, L. B.; Janda, K. D. J. Org. Chem. 2003, 68, 3673.
  4. Vaino, A. R.; Goodin, D. B.; Janda, K. D. J. Comb. Chem. 2000, 2, 330.
  5. Tois, J.; Koskinen, A. Tetrahedron Lett. 2003, 44, 2093.
  6. Choi, M.; Toy, P. H. Tetrahedron 2004, 60, 2903.
  7. Moss, J. A.; Dickenson, T. J.; Janda, K. D. Tetrahedron Lett. 2001, 42, 37.
  8. Brummer, O.; Clapham, B.; Janda, K. D. Tetrahedron Lett. 2001, 42, 2257.
  9. But, T.; Tashino, Y.; Togo, H.; Toy, P. H. Org. Biomol. Chem. 2005, 3, 970.
  10. Chung, C. W. Y.; Toy, P. H. Tetrahedron 2005, 61, 709.
  11. Choi, M.; Toy, P. H. Tetrahedron 2004, 60, 2875.
  12. Gilbertson, S. Yamada, S. Tetrahedron 2004, 45, 3917.
  13. Nogami, H.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 279.
  14. Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801.
  15. Song, C. E.; Yang, J. W.; Roh, E. J.; Lee, S.-G.; Ahn, J. H.; Han, H. Angew. Chem., Int. Ed. Engl. 2002, 41, 3852.
  16. Selkala, S. A.; Tois, J.; Petri, M.; Koskinen, A. Adv. Syn. Cat. 2002, 344, 941.
  17. Reger, T. S.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 6929.
  18. Toy, P. H.; Reger, T. S.; Garibay, P.; Garno, J. C.; Malikayil, J. A.; Liu, G.-Y.; Janda, K. D. J. Comb. Chem. 2001, 3, 117.
  19. Lee, S.-H.; Matsushita, H.; Koch, G.; Zimmerman, J.; Clapham, B.; Janda, K. D. J. Comb. Chem. 2004, 6, 822.
  20. Garibay, P.; Toy, P. H.; Hoeg-Jensen, T.; Janda, K. D. Synlett 1999, 9, 1438.
  21. Matsushita, H.; Lee, S.-H.; Joung, M.; Clapham, B. Janda, K. D. Tetrahedron Lett. 2004, 45, 313.
  22. Fujimori, T.; Wirsching, P.; Janda, K. D. J. Comb. Chem. 2003, 5, 625.
  23. Clapham, B.; Lee, S.-H.; Koch, G.; Zimmerman, J.; Janda, K. D. Tetrahedron Lett. 2002, 43, 5407.

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