Asymmetric reactions on polymers: Diastereoselective allylation of polymer-supported chiral imines

New Journal of Chemistry

Volumn 22, Issue 8, 1998, Pages 775-777

  Itsuno, Shinichi ^a   El Shehawy, Ashraf A ^a,c   Abdelaal, Magdy Y ^b   Ito, Koichi ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b Mansoura University   (Egypt)

^c TANTA UNIVERSITY   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001240182     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803375g     Document Type: Article

References (15)

1. For reviews on polymer-supported reagents and catalysts, see: (a) S. Itsuno, in Polymeric Materials Encyclopedia: Synthesis, Properties and Applications, ed. J. C. Salamone, CRC Press, Boca Raton, FL, 1996, vol. 10, pp. 8078-8087;
2. (b) S. Itsuno, in Macromolecules 1992, ed. J. Kahovec, VSP, Utrecht, 1993, pp. 413-422;
3. (c) E. C. Blossey and W. T. Ford, in Comprehensive Polymer Science, ed. G. Allen, Pergamon, Oxford, 1989, vol. 6, pp. 81-114;
4. (d) Synthesis and Separations Using Functional Polymers, ed. D. C. Sherrington and P. Hodge, Wiley, Chichester, 1988.
5. M. Cernerud, J. A. Reina, J. Tegenfeldt and C. Moberg, Tetrahedron: Asymmetry, 1996, 7, 2863.
6. (a) M. Calmes, J. Daunis, R. Jacquier, G. Nkusi, J. Verducci and P. Viallefont, Tetrahedron Lett., 1986, 4303;
7. (b) M. Kawana and S. Emoto, Tetrahedron Lett., 1972, 4855;
8. (c) A. R. Colwell, L. R. Duckwall, R. Brooks and S. P. McManus, J. Org. Chem., 1981, 46, 3097.
9. (a) T. Basile, A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Org. Chem., 1994, 59, 7766;
10. (b) A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Chem. Soc., Chem. Commun., 1993, 1542;
11. (c) A. Bocoum, C. Boga, D. Savoia and A. Umani-Ronchi, Tetrahedron Lett., 1991, 32, 1367.
12. 4a The configuration of the obtained homoallylamines 2b and 2c is estimated to be (S, S) from the results obtained from the allylation of benzaldimine.
13. 1H NMR spectrum to that obtained in Scheme 3.
14. Methine protons α to the tester group in 5, 11a and 11b appear at 2.70, 2.75 and 2.80 ppm, respectively, for the (S, S) isomer. Peaks for the (R, S) isomers appear at around 3.0 ppm.
15. Enantiomeric excesses were determined by HPLC using a chiral stationary phase [Daicel Chiralcel OD-H, hexane-isopropyl alcohol-diethylamine (90:10:0.1)].