An efficient synthesis of 3(S)-aminopiperidine-5(R)-carboxylic acid as a cyclic β,γ′-diamino acid

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1611-1614

  Park, Jin Seong ^a   Yeom, Chang Eun ^a   Choi, Soo Hyuk ^a   Ahn, Yong Shik ^a   Ro, Sunggu ^b,c   Jeon, Young Ho ^b,c   Shin, Dong Kyu ^b,c   Kim, B Moon ^a  

^a Seoul National University   (South Korea)

^b LG Chemical Ltd   (South Korea)

^c CrystalGenomics Inc   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DIAMINO ACID; ESTER DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; ENANTIOMER; HYDROLYSIS; SYNTHESIS;

EID: 0037450385     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00002-9     Document Type: Article

References (44)

1. For a review, see: (a) Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wiley: New York, 1995; Vol. I, pp. 803-861;
2. (b) Creighton, T. E. Proteins: Structure and Molecular Properties, 2nd ed.; Freeman: New York, 1993.
3. For example, see: (a) Feigel, M.; Brandmeier, V.; Bremer, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 486;
4. (b) Callahan, J. F.; Bean, J. W.; Burgess, J. L.; Eggleston, D. S.; Hwang, S. M.; Kopple, K. D.; Koster, P. F.; Nichols, A.; Peishoff, C. E.; Samanen, J. M.; Vasko, J. A.; Wong, A.; Huffman, W. F. J. Med. Chem. 1992, 35, 3970;
5. (c) Kemp, D. S.; Carter, J. S. J. Org. Chem. 1989, 54, 109;
6. (d) Smith, A. B.; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1992, 114, 10672;
7. (e) Gardner, B.; Nakanishi, H.; Kahn, M. Tetrahedron 1993, 49, 3433.
8. Kim, B. M.; Shaw, A. W.; Graham, S. L.; deSolms, J. S.; Ciccarone, T. M. US Patent 5,817,678, Oct. 6, 1998.
9. Angenot L., Dideberg O., Dupont L. Tetrahedron Lett. 16:1975;1357-1358.
10. Benson W., Winterfeldt E. Heterocycles. 15:1981;935-941.
11. Danieli B., Lesma G., Mauro M., Palmisano G. Bergman J., Van der Plas H.C., Somonyi M. Chemoenzymatic Approach to some Indole Alkaloids: Heterocycles in Bioorganic Chemistry. 1991;28-53 Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso-Compounds; 1993; Vol. 1, pp. 143-219.
12. For some recent examples, see: (a) Schneider, J. P.; Kelly, J. W. J. Am. Chem. Soc. 1995, 117, 2533;
13. (b) Gardner, R. R.; Liang, G. B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280;
14. (c) Nowick, J. S.; Mahrus, S.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 1066;
15. (d) Das, C.; Raghothama, S.; Balaram, P. J. Am. Chem. Soc. 1998, 120, 5812;
16. (e) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287;
17. (f) Nowick, J. S.; Chung, D. M.; Maitra, K.; Maitra, S.; Stigers, K. D.; Sun, Y. J. Am. Chem. Soc. 2000, 122, 7654;
18. (g) Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443;
19. (h) Nowick, J. S.; Cary, J. M.; Tsai, J. H. J. Am. Chem. Soc. 2001, 123, 5176.
20. For representative examples, see: (a) Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooks, J. R.; Saperstein, R. Science, 1980, 210, 656;
21. (b) Kemp, D. S.; Sun, E. T. Tetrahedron Lett. 1982, 23, 3759;
22. (c) Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647;
23. (d) Kahn, M.; Wilke, S.; Chen, B.; Fujita, K. J. Am. Chem. Soc. 1988, 110, 1638;
24. (e) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437;
25. (f) Slomczynsks, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198;
26. (g) Jean, F.; Buisine, E.; Melnyk, O.; Drobecq, H.; Odaert, B.; Hugues, M.; Lippens, G.; Tartar, A. J. Am. Chem. Soc. 1998, 120, 6076;
27. (h) Jones, I. G.; Jones, W.; North, M. J. Org, Chem. 1998, 63, 1505;
28. (i) Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C.; Piarulli, U.; Manzoni, L. Eur. J. Org. Chem. 1999, 379;
29. (j) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806;
30. (k) Jiménez, A. I.; Cativiela, C.; Marraud, M. Tetrahedron Lett. 2000, 41, 5353.
31. Danieli B., Lesma G., Passarella D., Silvani A. Synth. Commun. 27:1997;69.
32. Danieli B., Lesma G., Passadrella D., Silvani A. Tetrahedron: Asymmetry. 7:1996;345.
33. Danieli B., Lesma G. J. Org. Chem. 63:1998;3492.
34. For a review of enzymatic kinetic resolution, see: (a) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, 1995;
35. (b) Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: New York, 1992;
36. (c) Farber, K. Biotransformations in Organic Chemistry; Springer-Verlag: New York, 1992.
37. (d) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
38. For a review of α-PEA application to enantioselective synthesis: Juaristi, E.; Escalante, J.; León-Romo, J. L.; Reyes, A. Tetrahedron: Asymmetry 1998, 9, 715.
39. 6 [M+1] 302.1604, found 302.1605.
40. 4, filtered and concentrated to afford the partially resolved cis-4 (96% yield, 28% ee) as a white solid.
41. 6 [M+1] 288.1447, obsd 288.1441.
42. Preparation of (-)-cis-4 was possible through employing (R)-(+)-PEA following the same fractional crystallization process.
43. 4, THF.
44. Haefliger W., Klöppner E. Helv. Chim. Acta. 65:1982;1837.