Simple Three-Step Synthesis of (R)- And (S)-4-Amino-3-hydroxybutanoic Acid (GABOB) by Stereoselective Aldol Addition

Synthesis (Germany)

Volumn 1989, Issue 11, 1989, Pages 856-858

  Braun, Manfred ^a   Waldmüller, Delia ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

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Indexed keywords

EID: 84986671973     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1989-27410     Document Type: Article

References (29)

1. Index, M. Windholz (ed. ), 10th ed., Merck & Co, Inc., Rahway, 1983. Pharmazeutische Stoffliste, Aizneibiiro der Bundesvereinigung deutscher Apothekerverbande (ed. ), 7th extended edition, Frankfurt/Main, 1988.
2. Kaneko, T, Yoshida, R. Bull. Chem. Soc. Jpn. 1962, 35, 1153.
3. See textbooks on biochemistry, e. g. Lehninger, A. L. Prinzipien der Biochemie, de Gruyter, Berlin 1987, p. 566.
4. Fritz, I. B., Schultz, S. K. Biol. Chem. 1965, 240, 2188.
5. Borum, P. R. Nutr. Rev. 1981, 39, 385;
6. Tomita, M., Sendju, Y. Z. Physiol. Chem. 1927, 169, 263.
7. Hanessian, S. Total Synthesis oj Natural Products: The 'Chiron' Approach, Pergamon Press, Oxford, 1983.
8. Jung, M. E., Shaw, T. J. J. Am. Chem. Soc. 1980, 102, 6304.
9. Bock, K., Ludt, I., Pedersen, C. Acta Chem. Scand. B. 1983, 37, 341.
10. Rajaskhar, B., Kaiser, E. T. J. Org. Chem. 1985, 50. 5480.
11. Renaud, P., Seebach, D. Synthesis 1986, 424.
12. Rossiter, B. E., Sharpless, K. B. J. Org. Chem. 1984, 49, 3707.
13. Kitamura, M., Ohkuma, T., Takaya, H., Noyori, R. Tetrahedron Lett. 1988, 29, 1555.
14. Zhou, B., Gopalan, A. S. Van Middlesworth, F, Shieh, W. R., Sih, C. J. J. Am. Chem. Soc. 1983, 105, 5925.
15. Seebach, D., Zfiger, M. F., Giovannini, F, Sonnleitner, B., Ficch-ter, A. Angew. Chem. 1984, 96, 155;
16. Angew. Chem. Int. Ed. Engl. 1984, 23, 151.
17. Fuganti, C, Grasselli, P. Tetrahedron Lett. 1985, 26, 101.
18. Gopalan, A. S., Sih, C. J. Tetrahedron Lett. 1984, 25, 5235.
19. Dropsy, E. P., Klibanov Biotechn. Bioeng. 1984, 26, 9. 11.
20. Bianchi, D., Cabri, W., Cesti, P., Francalanci, F, Ricci, M. Org. Chem. 1988, 53, 104.
21. Braun, M. Angew. Chem. 1987, 99, 24;
22. Angew. Chem. Int. Ed. Engl. 1987, 26, 24.
23. Mahler, U., Devant, R. M., Braun, M. Chem. Ber. 1988, 121, 2035.
24. R- A nd (S)-HYTRA are commercially available from Merck-Schuchardt; see: MS INFO 1988, 88-4.
25. Dale, J. A., Dull, D. L., Mosher, H. S. Org. Chem. 1969, 34, 2543
26. Schreiber, S. L., Kellv, S. E., Porco, Jr., J. A Sammakia, X, Suh, E. M. J. Am. Chem. Soc. 1988, 110, 6210.
27. Devant, R., Mahler, U., Braun, M. Chem. Ber. 1988, 121, 397.
28. C. Fehrentz, J.-A., Castro, B. Synthesis 1983, 676.
29. Bischofberger. N, Waldmann, H., Saito, T, Simon, E. S., Lees, W., Bednarski, M. D. Whitesides, G. M. J. Org. Chem. 1988,. 55, 3457.