Highly selective chiral recognition on polymer supports: preparation of a combinatorial library of dihydropyrimidines and its screening for novel chiral HPLC ligands

Abstract

A library of more than 140 racemic 4-aryl-1,4-dihydropyrimidines has been synthesized using the single step Biginelli multicomponent condensation; the individual compounds were screened for enantiomer resolution, and the best candidate attached to a solid macroporous polymer support to afford a highly selective separation medium for chiral HPLC.

References

1. Combinatorial Chemistry, Synthesis and Application, ed. S. R. Wilson and A. W. Czarnik, Wiley, New York, 1997.
2. B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper and A. H. Hoveyda, Angew. Chem., Int. Ed. Engl., 1996, 35, 1668.
3. S. Brocchini, K. James, V. Tangpasuthadol and J. Kohn, J. Am. Chem. Soc., 1997, 119, 4553.
4. L. C. Hsieh-Wilson, X. D. Xiang and P. G. Schultz, Acc. Chem. Res., 1996, 29, 164.
5. T. A. Dickinson and D. R. Walt, Anal. Chem., 1997, 69, 3413.
6. P. Y. Huang and R. G. Carbonell, Biotechnol. Bioeng., 1995, 47, 288.
7. Y. Cheng, T. Suenaga and W. C. Still, J. Am. Chem. Soc., 1996, 118, 1813.
8. Chiral Separations, Applications and Technology, ed. S. Ahuja, ACS, Washington D.C., 1997.
9. W. H. Pirkle and T. C. Pochapsky, Chem. Rev., 1989, 89, 347.
10. W. H. Pirkle, D. W. House and J. M. Finn, J. Chromatogr., 1980, 192, 143.
11. K. Lewandowski, F. Svec and J. M. J. Fréchet, Chem. Mater., 1998, 10, 385.
12. K. Lewandowski, P. Murer, F. Svec and J. M. J. Fréchet, Anal. Chem., 1998, 10, 1629.
13. P. Biginelli, Gazz. Chim. Ital., 1893, 23, 360.