Preparation of polyamino acid catalysts for use in Julia asymmetric epoxidation

Chirality

Volumn 9, Issue 2, 1997, Pages 198-202

  Bentley, P A ^a   Kroutil, W ^a   Littlechild, J A ^b   Roberts, S M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

amino acid N carboxyanhydride; oligopeptide

Indexed keywords

POLYAMINOACID;

AMINO TERMINAL SEQUENCE; CATALYST; CONFERENCE PAPER; CROSS LINKING; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; PEPTIDE SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030998044     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:2<198::AID-CHIR22>3.0.CO;2-H     Document Type: Conference Paper

References (18)

1. Ehler, K.W., Orgel, L.E. N, N′-Carbonyldiimidazole Induced Peptide Formation in Aqueous Solution, Biochim. Biophys. Acta 434:233-243, 1976.
2. Ferris, J.P., Hill, Jr., A.R., Lui, R., Orgel, L.E. Synthesis of long prebiotic oligomers on mineral surfaces, Nature 381:59-61, 1996.
3. Akabori, S., Sakurai, S., Izumi, Y., Fujii, Y. An Asymmetric Catalyst, Nature 323-324, 1956.
4. Tsuboyama, S. Catalytic Asymmetric Cyanohydrin Synthesis with Synthetic Optically Active Polymer. I. Synthesis of Benzaldhyde Cyanohydrin. Bull. Chem. Soc. Jpn. 35:1004-1010, 1962.
5. Juliá, S., Masana, J., Vega, J.C. "Synthetic enzymes". Highly Stereoselective Epoxidation of Chalcone in a Triphasic Toluene-Water-Poly[(S)-alanine] System, Angew. Chem. Int. Ed. Engl. 19:929-930, 1980.
6. Juliá, S., Guixer, J., Masana, J., Rocas, J., Colonna, S., Annuziata, R., Molinari, H. Synthetic enzymes. Part 2. Catalytic Asymmetric Epoxidation by means of Polyaminoacids in a Triphasic System. J. Chem. Soc. Perkin 1 1317-1324, 1982.
7. Colonna, S., Molinari, H., Banfi, S., Juliá, S., Masana, J., Alvarez, A. Synthetic enzymes-Part 4. Highly Enantioselective Epoxidation by means of Polyaminoacids in a Triphasic System: Influence of Structural Variations within the Catalyst, Tetrahedron 39:1635-1641, 1983.
8. Banfi, S., Colonna, S., Molinari, H., Juliá, S., Guixer, J. Asymmetric Epoxidation of Electron Poor-Olefins. 5 Influence on Stereoselectivity of the Structure of Poly-α-Aminoacids used as Catalysts, Tetrahedron 40:5207-5211, 1984.
9. Flisak, J.R., Gombatz, K., Holmes, M.M., Jarmas, A.A., Lantos, I., Mendelson, W., Norack, V.J., Remich, J.J., Snyder, L. A Practical, Enantioselective Synthesis of SK&F 104353, J. Org. Chem. 58:6247-6254, 1993.
10. Augustyn, J.A.N., Bezuidenhoudt, B.C.B., Ferreira, D. Enantioselective Synthesis of Flavonoids. Part 1. Poly-Oxygenated Chalcone Epoxides, Tetrahedron 46:2651-2660, 1990.
11. Lasterra-Sánchez, M.E., Roberts, S.M., Enantiocomplementary asymmetric epoxidation of selected enones using poly-L-leucine and poly-D-leucine, J. Chem. Soc. Perkin 1 1467-1468, 1995.
12. Lasterra-Sánchez, M.E., Felfer, U., Mayon, P., Roberts, S.M., Thornton, S.R., Todd, C.J. Development of the Juliá Asymmetric Epoxidation Reaction. Part 1. Application of the Oxidation to Enones Other than Chalcone, J. Chem. Soc. Perkin 1 343, 1996.
13. Kroutil, W., Mayon, P., Lasterra-Sánchez, M.E., Maddrell, S., Roberts, S.M., Thornton, S.R., Todd, C.J., Tüter, M. Unexpected asymmetric epoxidation reactions catalysed by Poly-leucine-based systems, J. Chem. Soc. Chem. Commun. 845-846, 1996.
14. Kricheldorf, H.R. α-Aminoacid-N-Carboxy-Anhydrides and Related Heterocycles. Berlin: Springer-Verlag, 1987.
15. Perrin, D.D., Armarego, W.L.F. Purification of laboratory Chemicals, 2nd ed. Oxford: Pergamom Press, 1980.
16. Marsman, B., Wynberg, H. Absolute Configuration of Chalcone Epoxide. Chemical Correlation, J. Org. Chem. 44:2312-2314, 1979.
17. Itsuno, S., Sakakura, M., Ito, K. Polymer-Supported Poly (amino acids) as New Asymmetric Epoxidation Catalysts of α,β-Unsaturated Ketones, J. Org. Chem. 55:6047-6049, 1990.
18. Yoder, M.D., Keen, N.T., Jurnak, J. New Domain Motif: The Structure of Pectate Lyase C, a Secreted Plant Virulence Factor, Science 260: 1503-1507, 1993.