Chiral lipophilic ligands. 5. Enantioselective ester cleavage of α-amino esters by Cu(II) complexes of chiral diamino alcohols in aqueous surfactants solutions

Tetrahedron

Volumn 53, Issue 1, 1997, Pages 357-368

  Cleij, Marco C ^a   Mancin, Fabrizio ^a   Scrimin, Paolo ^b   Tecilla, Paolo ^a   Tonellato, Umberto ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; DRUG SYNTHESIS; HYDROLYSIS; PRIORITY JOURNAL; TECHNIQUE;

EID: 0031060342     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00991-X     Document Type: Article

References (37)

1. a) Fendler, J. Membrane Mimetic Chemistry, Wiley, New York, 1982;
2. b) Fendler, J. H.; Fendler, J. E. Catalysis in Micellar and Macromolecular Systems, Academic Press, New York, 1975.
3. a) Fornasier, R.; Tonellato, U. J. Chem. Soc., Faraday Trans. 1980, 76, 1301;
4. b) Bunton, C. A.; Savelli, G. Adv. Phys. Org. Chem. 1986, 22, 213;
5. c) Bunton, C. A.; Nome, F.; Quina, F. H.; Romsted, L. Acc. Chem. Res. 1991, 24, 357;
6. d) Menger, F. M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1086.
7. a) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. Recl. Trav. Chim. Pays - Bas 1992, 111 , 459;
8. b) Ueoka, R.; Matsumoto, Y.; Moss, R. A.; Swarup, S.; Sugii, A.; Harada, K.; Kikuchi, J.; Murakami, Y. J. Am. Chem. Soc. 1988, 110 , 1588;
9. c) Matsumoto, Y.; Ueoka, R. J. Org. Chem. 1990, 55, 5797;
10. d) Ohkubo, K.; Kawata, M.; Orito, T.; Ishida, H. J. Chem. Soc., Perkin Trans. 1 1989, 666;
11. e) Ihara, Y.; Asakawa, S.; Igata, K.; Matsumoto, Y.; Ueoka, R. J. Chem. Soc., Perkin Trans. 2 1991, 543.
12. Fornasier, R.; Milani, D.; Scrimin, P.; Tonellato, U. Gazz. Chim. Ital. 1986, 116, 55. Scrimin, P.; Tonellato, U. in "Surfactant in Solutions", Mittal, K.L.; Shah, D.O. Eds, Plenum Press, NY, 1991, Vol. 11, p. 349.
13. Fornasier, R.; Milani, D.; Scrimin, P.; Tonellato, U. Gazz. Chim. Ital. 1986, 116, 55. Scrimin, P.; Tonellato, U. in "Surfactant in Solutions", Mittal, K.L.; Shah, D.O. Eds, Plenum Press, NY, 1991, Vol. 11, p. 349.
14. a) Gellman, S.H.; Petter, R.; Breslow, R. J. Am. Chem. Soc. 1986, 108, 2388;
15. b) Menger, F. M.; Gan, L.H.; Johnson, E.; Durst, D. H. J. Am. Chem. Soc. 1987, 109, 2800;
16. c) Weijnen, J.G.J.; Koudijs, A.; Engbersen, J.F.J J. Org. Chem. 1992, 57, 7258;
17. d) Ogino, K.; Kashihara, N.; Ueda, T.; Isaka, T.; Yoshida, T.; Tagaki, W. Bull. Chem. Soc. Jpn. 1992, 65, 373;
18. e) Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1994, 59, 18;
19. f) Bunton, C. A.; Scrimin, P.; Tecilla, P. J. Chem. Soc., Perkin Trans. 2 1996, 419;
20. g) Kriste, A. G.; Vizitiu, D.; Thatcher, R. J. Chem. Commun. 1996, 913.
21. Scrimin, P.; Tecilla, P.; Tonellato, U. in "Organic Reactivity: Physical and Biological Aspects", Golding, B. T.; Griffin, R. J.; Maskill, H. Eds, The Royal Society of Chemistry, Cambridge, UK, 1995.
22. a) Cleij, M. C.; Tecilla, P.; Tonellato, U.; Scrimin, P. Gazz. Chim. Ital. in press;
23. b) Cleij, M. C.; Langmuir 1996, 12, 2956;
24. c) Scrimin, P.; Tecilla, P.; Tonellato, U. Tetrahedron 1995, 51, 217;
25. d) Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1994, 59, 4194.
26. Sigman, D. S.; Jorgensen, C. T. J. Am. Chem. Soc. 1972, 94, 1724.
27. Smith, R. M.; Martell, A. E., Critical Stability Costants, Plenum Press, New York, 1975, vol. 2.
28. Scrimin, P.; Tecilla, P.; Tonellato, U.; Vendrame, T. J. Org. Chem. 1989, 54, 5988.
29. Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1991, 56, 161.
30. Hathaway, B. J. in Comprehensive Co-ordination Chemistry, Wilkinson, G.; Gillard, R. D.; McCleverty, A. Eds., Pergamon Press, Oxford, 1987, Vol. 5, p.596-634.
31. a) Nakon, R.; Angelici, R. J. J. Am. Chem. Soc. 1974, 96, 4178;
32. b) Sigel, H.; Martin, R. B. Chem. Rev. 1982, 82, 385.
33. Holzbecher, Z. Handbook of Organic Reagents in Inorganic Analysis ; Wiley, Chichester, 1976.
34. Good, N. E.; Winget, G. D.; Winter, W.; Connolly, T. N.; Izawa, S.; Singh, R. M. M. Biochemistry 1966, 5 , 467.
35. Duynstee, E. F. J.; Grunwald, E. J. Am. Chem. Soc. 1959, 81 , 4540.
36. Ingles, D. W.; Knowles, J. R. Biochem, J. 1967, 104 , 369.
37. Welch, J. T.; Seper, K. W. J. Org. Chem. 1988, 53, 2991.