Synthesis of difluorinated pseudopeptides using chiral α,α- difluoro-β-amino acids in the Ugi reaction

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 773-776

  Gouge, Vanessa ^a   Jubault, Philippe ^a   Quirion, Jean Charles ^a  

^a IRCOF   (France)

Author keywords

Phenylglycinol; Pseudopeptides; Ugi reaction; , Difluoro amino acids

Indexed keywords

2,2 DIFLUORO 3 (2 HYDROXY 1 PHENYLETHYLAMINO) 3 PHENYLPROPIONIC ACID; 2,4 DIPHENYLOXAZOLIDINE; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; ETHYL BROMODIFLUOROACETATE; FLUOROACETIC ACID; OXAZOLIDINE DERIVATIVE; PSEUDOPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DEPROTECTION REACTION; DRUG SYNTHESIS; FLUORINATION; HYDROGENOLYSIS; UGI REACTION;

EID: 0346787853     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.019     Document Type: Article

References (29)

1. (a) Ugi I. Angew. Chem., Int. Ed. 21:1982;810-819
2. (b) Ugi I. J. Prakt. Chem. 339:1997;499-516
3. (c) Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3168-3210.
4. (a) Mjalli A.M.M., Sarshar S., Baiga T.J. Tetrahedron Lett. 37:1996;2943-2946
5. (b) Hanusch-Kompa C., Ugi I. Tetrahedron Lett. 39:1998;2725-2728
6. (c) Short K.M., Mjalli A.M.M. Tetrahedron Lett. 38:1997;359-362
7. (d) Short K.M., Ching B.W., Mjalli A.M.M. Tetrahedron Lett. 39:1998;7489-7492
8. (e) Bienayme H., Bouziuo K. Tetrahedron Lett. 39:1998;2735-2738
9. (f) Hulme C., Morissette M.W., Volz F.A., Burns C.J. Tetrahedron Lett. 39:1998;1113-1116
10. (g) Hulme C., Ma L., Cherrier M.-P., Romano J.J., Morton G., Duquenne C., Salvino J., Labaudiniere R. Tetrahedron Lett. 41:2000;1883-1887
11. (h) Hulme C., Ma L., Vasant Kumar N., Krolikowski P.H., Allen A.C., Labaudiniere R. Tetrahedron Lett. 41:2000;1509-1514
12. (i) Nixey T., Tempest P., Hulme C. Tetrahedron Lett. 43:2002;1637-1639
13. (j) Kennedy A.L., Fryer A.M., Josey J.A. Org. Lett. 4:2002;1167-1170.
14. (a) Keating T.A., Armstrong R.W. J. Am. Chem. Soc. 118:1995;2574-2583
15. (b) Keating T.A., Armstrong R.W. J. Org. Chem. 61:1996;8935-8939
16. Linderman R.J., Binet S., Petrich S.R. J. Org. Chem. 64:1999;336-337.
17. Ojima I., McCarthy J.R., Welch J.T. Biomedical Frontiers of Fluorine Chemistry. ACS Symposium Series 369. 1996;American Chemical Society, Washington, DC.
18. (a) Iseki K. Tetrahedron. 54:1998;13887-13914
19. (b) Tozer M.J., Herpin T.F. Tetrahedron. 52:1996;8619-8683.
20. Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;VCH-Wiley, New York.
21. Matthews J.L., Overhand M., Kühnle F.N.M., Ciceri P.E., Seebach D. Liebigs Ann. Recl. 1997;1371-1381.
22. (a) Hart D.J., Ha D.-C. Chem. Rev. 89:1989;1447-1465
23. (b) Van der Steen F.H., Van Koten G. Tetrahedron. 47:1991;7503-7524.
24. (a) Marcotte S., Pannecoucke X., Feasson C., Quirion J.-C. J. Org. Chem. 64:1999;8461-8464
25. (b) For recent modified approaches, see: Staas D.D., Savage K.L., Homnick C.F., Tsou N.N., Ball R.G. J. Org. Chem. 67:2002;8276-8279 Vidal A., Nefzi A., Houghten R.A. J. Org. Chem. 66:2001;8268-8272.
26. (b) For recent modified approaches, see: Staas D.D., Savage K.L., Homnick C.F., Tsou N.N., Ball R.G. J. Org. Chem. 67:2002;8276-8279 Vidal A., Nefzi A., Houghten R.A. J. Org. Chem. 66:2001;8268-8272.
27. (2-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methylxy-1R- phenylethylamino)-3S-phenylpropionyl]-aminot-butyl ester 5m : All compounds were diluted in dry MeOH to afford a concentration of approximately 1 M. N-Boc-phenylenediamine (112 mg, 0.54 mmol, 1.2 equiv) and benzaldehyde (0.069 mL, 0.675 mmol, 1.5 equiv) were combined and the reaction was stirred for 2 h. Isonitrile (167 mg, 0.675 mmol, 1.5 equiv) and 2,2-difluoro-3-(2-hydroxy-1 R-phenylethylamino)-3 S-phenylpropionic acid (286 mg, 0.45 mmol, 1 equiv) were added, and the reaction was stirred for 24 h. After the solvent had been evaporated, the residue was purified on silica gel, eluting with cyclohexane/ethyl acetate gradient (9/1 to 7/3).
28. (a) Bock H., Ugi I. J. Prakt. Chem. 339:1997;385-389
29. (b) Ziegler T., Schlomer R., Koch O. Tetrahedron Lett. 39:1998;5957-5960.