Immobilization of TADDOL with a high degree of loading on porous silica gel and first applications in enantioselective catalysis

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 163-165

  Heckel, Alexander ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Asymmetric catalysis; Cyclo additions; Immobilization; Lewis acids; Nucleophilic additions

Indexed keywords

ACID; SILICA GEL; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; ENANTIOMER; IMMOBILIZATION; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0034598508     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<163::AID-ANIE163>3.0.CO;2-J     Document Type: Article

References (28)

1. a) W. Keim, B. Driessen-Hölscher in Handbook of Heterogeneous Catalysis, Vol. 1 (Eds.: G. Ertl, H. Knözinger, J. Weitkamp), Wiley-VCH, Weinheim, 1997, pp. 231-240;
2. b) M. T. Reetz, A. Zonta, J. Simpelkamp, Angew. Chem. 1995, 107, 373-376; Angew. Chem. Int. Ed. Engl. 1995, 34, 301-303.
3. b) M. T. Reetz, A. Zonta, J. Simpelkamp, Angew. Chem. 1995, 107, 373-376; Angew. Chem. Int. Ed. Engl. 1995, 34, 301-303.
4. H. U. Blaser, B. Pugin in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, pp. 33-57, and references therein.
5. D. Seebach, R. E. Marti, T. Hintermann, Helv. Chim. Acta 1996, 79, 1710-1740, and references therein.
6. H. Sellner, D. Seebach, Angew. Chem. 1999, 111, 2039-2041; Angew. Chem. Int. Ed. 1999, 38, 1918-1920, and references therein.
7. H. Sellner, D. Seebach, Angew. Chem. 1999, 111, 2039-2041; Angew. Chem. Int. Ed. 1999, 38, 1918-1920, and references therein.
8. J. F. Biernat, P. Konieczka, B. J. Tarbet, J. S. Bradshaw, R. M. Izatt in Separation and Purification Methods, Vol. 23(2) (Eds.: P. C. Wankat, C. J. van Oss, J. D. Henry), Marcel Dekker, New York, 1994, pp. 77-348, and references therein.
9. A. Choplin, F. Quignard, Coord. Chem. Rev. 1998, 180, 1679-1702.
10. The CPG used was provided by Grace GmbH (In der Hollerhecke 1, D-67547 Worms, Germany (www.grace.com)) and has the following batch numbers: SP 2-8319.01 (200 Å), SP 18-9042 (500 Å).
11. J. N. Kinkel, K. K. Unger, J. Chromatogr. 1984, 316, 193-200.
12. K. D. McMurtrey, J. Liq. Chromatrogr. 1988, 11, 3375-3384.
13. a) G. L. Ellman, Arch. Biochem. Biophys. 1959, 82, 70-77;
14. b) R. D. Badley, W. T. Ford, J. Org. Chem. 1989, 54, 5437-5443.
15. B. S. Sproat, M. J. Gait in Oligonucleotide Synthesis. A practical approach (Ed.: M. J. Gait), IRL Press, Oxford, 1984, pp. 83-115.
16. K. V. Gothelf, I. Thomsen, K. A. Jørgensen, J. Am. Chem. Soc. 1996, 118, 59-64.
17. B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 1383-1385; Angew. Chem. Int. Ed. Engl. 1991, 30, 1321-1323.
18. B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 1383-1385; Angew. Chem. Int. Ed. Engl. 1991, 30, 1321-1323.
19. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
20. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
21. 2Zn to PhCHO.
22. 2/ZnO, but, rather, appears to have a positive effect on reproducibility (see right part of the curves in Figure 1).
23. Reviews: a) R. Dahinden, A. K. Beck, D. Seebach in Encyclopaedia of Reagents for Organic Synthesis, Vol. 3 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2167-2171;
24. b) H. Yamamoto, A. Yanagisawa, K. Ishihara, S. Saito, Pure Appl. Chem. 1998, 70, 1507-1512;
25. c) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed. Engl. 1997, 36, 1237-1256;
26. c) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed. Engl. 1997, 36, 1237-1256;
27. d) S. Kobayashi, Pure Appl. Chem. 1998, 70, 1019-1026;
28. e) K. Mikami, Pure Appl. Chem. 1996, 68, 639-644.