Enantioselective synthesis of α,α-disubstituted amino acid derivatives via enzymatic resolution: Preparation of a thiazolyl-substituted α-methyl α-benzyl amine

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7398-7401

  Spero, Denice M ^a   Kapadia, Suresh R ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PHENETHYLAMINE DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; DRUG PURIFICATION;

EID: 0029856073     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9610671     Document Type: Article

References (21)

1. For reviews see: (a) Jung, M. J. Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p 227. (b) α-Amino Acid Synthesis; O'Donnell, M. J., Ed.; Tetrahedron Symposium-in-Print; Pergamon: London, 1988; Vol. 44, Issue 17. (c) Williams, R. W. Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989.
2. For reviews see: (a) Jung, M. J. Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p 227. (b) α-Amino Acid Synthesis; O'Donnell, M. J., Ed.; Tetrahedron Symposium-in-Print; Pergamon: London, 1988; Vol. 44, Issue 17. (c) Williams, R. W. Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989.
3. For reviews see: (a) Jung, M. J. Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; p 227. (b) α-Amino Acid Synthesis; O'Donnell, M. J., Ed.; Tetrahedron Symposium-in-Print; Pergamon: London, 1988; Vol. 44, Issue 17. (c) Williams, R. W. Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989.
4. (a) Schollkopf, U.; Hausberg, H. H.; Hoppe, I.; Segal, M.; Reiter, U. Angew. Chem., Int. Ed. Engl. 1978, 77(2), 117.
5. (b) Seebach, D.; Fadel, A. Helv. Chim. Acta 1985, 68, 1243.
6. (c) Fitzi, R.; Seebach, D. Tetrahedron 1988, 44(17), 5227.
7. (d) Karady, S.; Amato, J. S.; Weinstock, L. M. Tetrahedron Lett. 1984, 25(39), 4337.
8. (e) Zydowsky, T. M.; de Lara, E.; Spanton, S. G. J. Org. Chem. 1990, 55, 5437.
9. (f) Cheng, H.; Keitz, P.; Jones, B. J. J. Org. Chem. 1994, 59, 7671.
10. (g) Davies, S. G.; Alonso, F. Tetrahedron Assymetry 1995, 6(2), 353.
11. Subramanian, P. K.; Woodard, R. W. Synth. Commun. 1986, 16(3), 337.
12. (a) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525.
13. (b) Liu, W.; Ray, P.; Benezra, S. A. J. Chem. Soc., Perkin Trans. 1 1995, 553.
14. Lipase L was purchased from Amano.
15. Nucleosil C18 reversed-phase column. Eluant = 1:1 acetonitrile/ water with 1% TFA.
16. Absolute configurations were determined by X-ray analysis of the final thiazolyl compounds.
17. 2NH.
18. Preparative Biotransformations; Roberts, S. M., Wiggins, K., Casy, G., Eds.; Wiley: University of Exeter, Exeter, U.K., 1992; Chapter 1.
19. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
20. The ee of the final product was confirmed to be 99.6% after derivatization and recrystallization.
21. Chromatographic conditions for each step are reported in the Experimental Section for characterization purposes only.