Search for Chiral Catalysts Through Ligand Diversity: Substrate-Specific Catalysts and Ligand Screening on Solid Phase

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 16, 1997, Pages 1704-1707

  Shimizu, Ken D ^a   Cole, Bridget M ^a   Krueger, Clinton A ^a   Kuntz, Kevin W ^a   Snapper, Marc L ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Asymmetric catalysis; Epoxides; Heterogeneous catalysis; Peptides; Solid phase synthesis

Indexed keywords

EID: 0030766272     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717041     Document Type: Article

References (23)

1. B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671.
2. B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671.
3. Recent advances in the application of combinatorial techniques in the discovery of chiral catalysts: a) F. M. Menger, A. V. Eliseev, V. A. Migulin, J. Org. Chem. 1995, 60, 6666-6667; b) G. Lin, J. A. Ellman, ibid. 1995, 60, 7712-7713; c) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478; d) K. Burgess, H. Lim, A. M. Porte, G. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222.
4. Recent advances in the application of combinatorial techniques in the discovery of chiral catalysts: a) F. M. Menger, A. V. Eliseev, V. A. Migulin, J. Org. Chem. 1995, 60, 6666-6667; b) G. Lin, J. A. Ellman, ibid. 1995, 60, 7712-7713; c) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478; d) K. Burgess, H. Lim, A. M. Porte, G. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222.
5. Recent advances in the application of combinatorial techniques in the discovery of chiral catalysts: a) F. M. Menger, A. V. Eliseev, V. A. Migulin, J. Org. Chem. 1995, 60, 6666-6667; b) G. Lin, J. A. Ellman, ibid. 1995, 60, 7712-7713; c) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478; d) K. Burgess, H. Lim, A. M. Porte, G. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222.
6. Recent advances in the application of combinatorial techniques in the discovery of chiral catalysts: a) F. M. Menger, A. V. Eliseev, V. A. Migulin, J. Org. Chem. 1995, 60, 6666-6667; b) G. Lin, J. A. Ellman, ibid. 1995, 60, 7712-7713; c) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478; d) K. Burgess, H. Lim, A. M. Porte, G. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222.
7. Recent advances in the application of combinatorial techniques in the discovery of chiral catalysts: a) F. M. Menger, A. V. Eliseev, V. A. Migulin, J. Org. Chem. 1995, 60, 6666-6667; b) G. Lin, J. A. Ellman, ibid. 1995, 60, 7712-7713; c) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478; d) K. Burgess, H. Lim, A. M. Porte, G. Sulikowski, Angew. Chem. 1996, 108, 192-194; Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222.
8. F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337.
9. F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337.
10. a) H. Nitta, D. Yu, M. Kudo, A. Mori, S. Inoue, J. Am. Chem. Soc. 1992, 114, 7969-7975, and references therein;
11. b) M. Hayashi, Y. Miyamoto, T. Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522.
12. Although the synthesis of all peptide combinations is straightforward, we are currently limited in our ability to evaluate efficiently every possible ligand for asymmetric induction. Studies aimed at developing strategies that address this issue are under way.
13. C. T. Dooley, R. A. Houghten, Life Sciences 1993, 52, 1509-1517.
14. Our initial efforts towards carrying out ligand screening on a solid support were unsuccessful [1].
15. R. Noyori, Asymmetric Catalysis in Organic Chemistry, Wiley, New York, 1994, pp. 346-364.
16. Although levels of selectivity on solid and in solution phases may correlate, they may not be reliable. This is particularly an issue if selectivites on solid phases are low (for example less than 15% ee). In such instances ranking of various catalyst systems in order of their effectiveness becomes increasingly dubious, since differences in selectivity are small.
17. 2O, and MeCN) indicated that the most selective and reproducible results were obtained in toluene.
18. C. Bolm in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Blackie Academic and Professional, London, 1996, pp. 9-26.
19. lig[%] = enantiomeric excess of the ligand, K = ratio of the initial rates of optically pure versus racemic ligands (K = 3 in this case)): K. Mikami, M. Terrada, Tetrahedron 1992, 48, 5671-5680.
20. A. Akelah, D. C. Sherrington, Chem. Rev. 1981, 81, 557-587.
21. 13C NMR, and IR spectrometry, high-resolution mass spectroscopy, or combustion analysis.
22. The effect of the glycine at AA 3 was originally not appreciated and therefore went unnoted [1].
23. FMOC-Gly-PAC resin (PerSeptive Biosystems; FMOC = 9-fluorenylmethyloxycarbonyl) may also be used to obtain similar results.