Immobilized catalysts in combinatorial chemistry

Current Opinion in Chemical Biology

Volumn 4, Issue 3, 2000, Pages 338-345

  Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOACETONITRILE; AMINOALCOHOL; KETONE DERIVATIVE; POLYMER; QUINOLINE DERIVATIVE;

CATALYST; CHEMICAL MODIFICATION; ORGANIC CHEMISTRY; REVIEW; SYNTHESIS;

EID: 0034032554     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(00)00097-1     Document Type: Review

References (29)

1. Terrett N.K. Combinatorial Chemistry. 1998;Oxford University Press, Oxford.
2. Thompson L.A., Ellman J.A. Synthesis and applications of small molecule libraries. Chem Rev. 96:1996;555-600.
3. Früchtel J.S., Jung G. Organic chemistry on solid supports. Angew Chem Int Ed Engl. 35:1996;17-42.
4. Terrett N.K., Gardner M., Gordon D.W., Kobylecki R.J., Steele J. Combinatorial synthesis - the design of compound libraries and their application to drug discovery. Tetrahedron. 51:1995;8135-8173.
5. Lowe G. Combinatorial chemistry. Chem Soc Rev. 37:1995;309-317.
6. Gallop M.A., Barrett R.W., Dower W.J., Fodor S.P.A., Gordon E.M. Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J Med Chem. 37:1994;1233-1251.
7. Gordon E.M., Barrett R.W., Dower W.J., Fodor S.P.A., Gallop M.A. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J Med Chem. 37:1994;1385-1401.
8. Kobayashi S. New methodologies for the synthesis of libraries. Chem Soc Rev. 1999;1-26. This paper summarizes recent advances in the field in detail.
9. Kobayashi S., Nagayama S.J. A polymer-supported scandium catalyst. Org Chem. 61:1996;2256-2257.
10. Kobayashi S., Nagayama S.J. A new methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polymer-supported scandium catalyst. J Am Chem Soc. 118:1996;8977-8978.
11. 3-catalyzed three components coupling reactions between aldehydes, amines, and alkenes. Efficient syntheses of pyridine and quinoline derivatives. Chem Lett. 1995;423-424.
12. Kobayashi S., Ishitani H., Nagayama S. Lanthanide triflate catalyzed imino Diels-Alder reactions; convenient syntheses of pyridine and quinoline derivatives. Synthesis. 1995;1195-1202.
13. Kobayashi S., Nagayama S., Busujima T. Polymer scandium-catalyzed three-component reactions leading to diverse amino ketone, amino ester, and amino nitrile derivatives. Tetrahedron Lett. 37:1996;9221-9224.
14. Donbrow M. Microcapsules and Nanoparticles in Medicine and Pharmacy. 1992;CRC Press, Boca Raton, Fl.
15. Kobayashi S. Scandium triflate in organic synthesis. Eur J Org Chem. 1999;15-27.
16. Kobayashi S. Rare earth metal trifluoromethanesulfonates as water-tolerant Lewis acid catalysts in organic synthesis. Synlett. 1994;689-701.
17. Marshman R.W. Rare earth triflates catalysts in organic synthesis. Aldrichimica Acta. 28:1995;77-84.
18. Kobayashi S., Nagayama S.J. A microencapsulated Lewis acid. A new type of polymer-supported Lewis acid catalyst of wide utility in organic synthesis. J Am Chem Soc. 120:1998;2985-2986. The first immobilized catalyst is introduced in this paper.
19. Nagayama S., Endo M., Kobayashi S. Microencapsulated osmium tetraoxide. A new recoverable and reusable polymer-supported osmium catalyst for dihydroxylation of olefins. J Org Chem. 63:1998;6094-6095.
20. Kobayashi S., Endo M., Nagayama S. Catalytic asymmetric dihydroxylation of olefins using a recoverable and reusable polymer-supported osmium catalyst. J Am Chem Soc. 121:1999;11229-11230.
21. Wai J.S.M., Markó I., Svendsen J.S., Finn M.G., Jacobsen E.N., Sharpless K.B. A mechanistic insight leads to a greatly improved osmium-catalyzed asymmetric dihydroxylation process. J Am Chem Soc. 111:1989;1123-1124.
22. Kolb H.C., Van Nieuwenhze M.S., Sharpless K.B. Catalytic asymmetric dihydroxylation. Chem Rev. 94:1994;2483-2549.
23. Annis D.A., Jacobsen E.N. Polymer-supported chiral Co(Salen) complexes: synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides. J Am Chem Soc. 121:1999;4147-4154. Efficient polymer-supported catalysts for hydrolytic kinetic resolution of terminal epoxides are described.
24. Seebach D., Marti R., Hintermann T. Polymer- and dendrimer-bounded Ti-TADDOLates in catalytic (and stoichiometric) enantioselective reactions: are pentacoordinate cationic Ti complexes the catalytically active species? Helv Chim Acta. 79:1996;1710-1740.
25. Sellner H., Seebach D. Dendritically cross-linking chiral ligands. high stability of a polystyrene-bound Ti-TADDOLate catalyst with diffusion control Angew Chem Int Ed Engl. 38:1999;1918-1920.
26. Hechel A., Seebach D. Immobilization of TADDOL with a high degree of loading on porous silica gel and first applications in enantioselective catalysis. Angew Chem Int Ed Engl. 39:2000;163-165.
27. Johannsen M., Jorgensen K.A., Zheng X-F., Hu Q-S., Pu L. A highly enantioselective hetero-Diels-Alder reaction catalyzed by chiral polybinaphthyl-aluminium complexes. J Org Chem. 64:1999;299-301.
28. Fujii A., Sodeoka M. Palladium diaqua and hydroxo complexes with polymer-supported BINAP ligands and their use for catalytic enantioselective reactions. Tetrahedron Lett. 40:1999;8011-8014.
29. Uozumi Y., Danjo H., Hayashi T. Palladium-catalyzed asymmetric allylic substitution in aqueous media using amphiphilic resin-supported MOP ligands. Tetrahedron Lett. 39:1998;8303-8306.