A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

Tetrahedron Asymmetry

Volumn 14, Issue 23, 2003, Pages 3639-3641

  Lee, Jae Mok ^a   Lim, Hyun Suk ^a   Seo, Kyung Chang ^a   Chung, Sung Kee ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ESTERIFICATION; OZONOLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 0344153836     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.009     Document Type: Article

References (27)

1. Kingston, D. G. I.; Jagtap, P. G.; Yuan, H.; Samala, L. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H.; Kirby, G. W., Eds.; Springer: Wien, New York, 2002; Vol. 84; pp. 53-225.
2. Nicolaou K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15.
3. Umezawa H., Aoyagi H., Suda H., Hamada M., Takeuchi T. J. Antibiot. 29:1976;97.
4. Aoyagi T., Tobe H., Suda H., Kojima F., Hamada M., Takeuchi T. J. Antibiot. 31:1978;636.
5. Mimoto T., Imai J., Kisanuki S., Enomoto H., Hattori N., Akaji K., Kiso Y. Chem. Pharm. Bull. 40:1992;2251.
6. Umemura E., Tsuchiya T., Umezawa S. J. Antibiot. 41:1988;530.
7. Hamamoto H., Mamedov V.A., Kitamoto M., Hayashi N.O., Tsuboi S. Tetrahedron: Asymmetry. 11:2000;4485.
8. Kayser M.M., Mihovilovic M.D., Kearns J., Feicht A., Stewart J.D. J. Org. Chem. 64:1999;6603.
9. Kang S.H., Kim C.M., Youn J.H. Tetrahedron Lett. 40:1999;3581.
10. Jost S., Gimbert Y., Greene A.E. J. Org. Chem. 62:1997;6672.
11. Cardillo G., Tomasini C. Chem. Soc. Rev. 1996;117.
12. Ambroise L., Jackson R.F.W. Tetrahedron Lett. 37:1996;2311.
13. Bunnage M.E., Davies S.G., Goodwin C.J. J. Chem. Soc., Perkin Trans. 1. 1994;2385.
14. Lee J.M., Lim H.S., Chung S.K. Tetrahedron: Asymmetry. 13:2002;343.
15. Chung S.K., Kang K.H. Tetrahedron: Asymmetry. 8:1997;3027.
16. Abiko A., Masamune S. Tetrahedron Lett. 37:1996;1077.
17. 3CN, and DIBAL to give syn/anti products in good chemical yields (68-99%) but moderate diastereoselectivities (52-85% de).
18. The paucity of examples of the direct preparation of α-keto esters from enones via oxidative cleavages such as ozonolysis in the literature may suggest that a further detailed study of this reaction might be warranted.
19. Marshall J.A., Garofalo A.W. J. Org. Chem. 58:1993;3675.
20. It is also conceivable that the reduction of α-keto esters 5 and 6 takes place in the H-bonded cyclic structure between the amino group and the ester group.
21. 3) δ 4.92.
22. 3), mp 141-142°C.
23. Gou D.M., Liu Y.C., Chen C.S. J. Org. Chem. 58:1993;1287.
24. Wuts P.G.M., Northuis J.M., Kwan T.A. J. Org. Chem. 65:2000;9223.
25. 3), mp 122-123.5°C.
26. Hanessian S., Sanceau J.Y. Can. J. Chem. 74:1996;621.
27. Sakaitani M., Ohfune Y. J. Am. Chem. Soc. 112:1990;1150.