Asymmetric synthesis of α-amino acids using polymer-supported Cinchona alkaloid-derived ammonium salts as chiral phase-transfer catalysts

Tetrahedron Asymmetry

Volumn 11, Issue 16, 2000, Pages 3277-3281

  Chinchilla, Rafael ^a   Mazón, Patricia ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; CINCHONA ALKALOID;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHIRALITY; DRUG BINDING; DRUG PURIFICATION; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0034714152     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00317-7     Document Type: Article

References (49)

1. (a) Amino Acids, Peptides and Proteins. In Specialist Periodical Reports; Chemical Society: London, 1968-1995; Vol. 1-28.
2. (b) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis - Construction of Chiral Molecules Using Amino Acids; John Wiley & Sons: New York, 1987.
3. (c) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989.
4. (d) Stammer, C. H. Tetrahedron 1990, 46, 2231-2254.
5. (e) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264.
6. (f) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917.
7. (g) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650.
8. (h) Burgess, K.; Ho, K.-K.; Mye-Sherman, D. Synlett 1994, 575-583.
9. (i) Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Synth. 1995, 173-187.
10. (j) North, M. Contemp. Org. Synth. 1996, 323-343.
11. (k) Studer, A. Synthesis 1996, 793-815.
12. (l) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
13. (m) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
14. (n) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599.
15. (o) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
16. (p) Abellán, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689-2697.
17. Phase-Transfer Catalysis; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997.
18. (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355.
19. (b) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. J. Org. Chem. 1991, 56, 5181-5192.
20. (c) O'Donnell, M. J.; Wu, S. Tetrahedron: Asymmetry 1992, 3, 591-594.
21. (d) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507-4518.
22. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
23. (b) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350.
24. (c) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846.
25. (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598.
26. (b) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388.
27. (c) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392.
28. (d) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 8671-8674.
29. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519-6520.
30. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov A.V., Parmár V.S., Kumar R., Kagan H.B. Tetrahedron: Asymmetry. 9:1998;851-857.
31. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Vyskocil S., Kagan H.B. Tetrahedron: Asymmetry. 10:1999;1723-1728.
32. (a) Kobayashi, N.; Iwai, K. J. Am. Chem. Soc. 1978, 100, 7021-7022.
33. (b) Inagaki, M.; Hiratane, J.; Yamamoto, Y.; Oda, J. Bull. Chem. Soc. Jpn. 1987, 60, 4121-4126.
34. (c) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157-1161.
35. (a) Hodge, P.; Khoshdel, E.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2205-2209.
36. (b) Hodge, P.; Khoshdel, E.; Waterhouse, J.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1985, 2327-2331.
37. (a) Hermann, K.; Wynberg, H. Helv. Chim. Acta 1977, 60, 2208-2212.
38. (b) Alvarez, R.; Hourdin, M.-A.; Cavé, C.; d'Angelo, J.; Chaminade, P. Tetrahedron Lett. 1999, 40, 7091-7094.
39. (a) Nandanan, E.; Sudalai, A.; Ravindranathan Tetrahedron Lett. 1997, 38, 2577-2580.
40. (b) Canali, L.; Song, E. S.; Sherrington, D. C. Tetrahedron: Asymmetry 1998, 9, 1029-1034.
41. (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633.
42. (b) Han, H.; Janda, K. D. Tetrahedron Lett. 1997, 38, 1527-1530.
43. Song, C. E.; Oh, C. R.; Lee, S. W.; Lee, S.; Canali, L.; Sherrington, D. C. Chem. Commun. 1998, 2435-2436.
44. 4) and evaporated in vacuo.
45. Chirasil-LVal (Chrompack), 1 min 85°C, 2°/min to 180°C. Reference racemic samples were prepared under the same reaction conditions but using tetrabutylammonium bromide as phase-transfer catalyst.
46. 2O hydrolysis of the imine function and further reaction with trifluoroacetic anhydride (Oppolzer, W.; Moretti, R.; Zhou, C. Helv. Chim. Acta 1994, 77, 2363-2380).
47. Prepared in 80% overall yield by reaction of glycine with thionyl chloride in the presence of isopropanol (Patel, R.; Price, S. J. Org. Chem. 1965, 30, 3575-3576), followed by treatment of the crude with benzophenone imine (O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666).
48. Prepared in 80% overall yield by reaction of glycine with thionyl chloride in the presence of isopropanol (Patel, R.; Price, S. J. Org. Chem. 1965, 30, 3575-3576), followed by treatment of the crude with benzophenone imine (O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666).
49. 2O) (Dictionary of Organic Compounds; Chapman & Hall: New York, 1982).