Exceptionally simple homologation of protected α- to β-amino acids in the presence of silica gel

Synthetic Communications

Volumn 35, Issue 21, 2005, Pages 2789-2794

  Koch, Karen ^a   Podlech, Joachim ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Amino acids; amino acids; Diazo compounds; Silica gel; Wolff rearrangement

Indexed keywords

ACETIC ACID ETHYL ESTER; ALPHA AMINO ACID; BETA AMINO ACID; BETA AMINO ACID METHYL ESTER; DIAZOKETONE; KETONE DERIVATIVE; METHANOL; SILICA GEL; SILVER DERIVATIVE; SILVER TRIFLUOROACETIC ACID; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; EVAPORATION; FILTRATION; PURIFICATION; SYNTHESIS; WOLFF REARRANGEMENT;

EID: 29144494881     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500290466     Document Type: Article

References (20)

1. (a) Seebach, D.; Kimmerlin, T.; Sebesta, R.; Campo, M. A.; Beck, A. K. How we drifted into peptide chemistry and where we have arrived at. Tetrahedron 2004, 60, 7455-7506;
2. (b) Seebach, D.; Beck, A. K.; Bierbaum, D. J. The world of β- and γ-peptides comprised of homologated proteinogenic amino acids and other component. Chem. Biodiversity 2004, 1, 1111-1239;
3. (c) Podlech, J. Preparation of enantiopure β-amino acids by homologation of α-amino acids. In Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley: Hoboken, NJ, 2005; pp. 93-106;
4. (d) Matthews, J. L. Synthesis of peptides based on β-amino acids. In Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, 2003; Vol. E22c, pp. 552-569.
5. Linder, M. R.; Steurer, S.; Podlech, J. (S)-3-(tert-Butoxycarbonylamino)- 4-phenylbutanoic acid. Org. Synth. 2002, 79, 154-164.
6. (a) Ye, T.; McKervey, M. A. Organic synthesis with α-diazocarbonyl compounds. Chem. Rev. 1994, 94, 1091-1160;
7. (b) Kirmse, W. 100 years of the Wolff rearrangement. Eur. J. Org. Chem. 2002, 2193-2256.
8. α-protected α-aminodiazoketones in presence substituted phenol as a method for the synthesis of 2,4,5-trichlorophenyl esters of Fmoc-/Boc-/Z-β-homoamino acid. Protein Pept. Lett. 2000, 7, 33-36;
9. α-urethane protected α-amino acids to their β-homologues with concomitant pentafluorophenyl ester formation. Lett. Pept. Sci. 2000, 7, 165-169.
10. Ellmerer-Müller, E. P.; Brössner, D.; Maslouh, N.; Takó, A. Synthesis of N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-protected (Fmoc) β-amino acids (=homo-α-amino acids) by direct homologation. Helv. Chim. Acta 1998, 81, 59-65.
11. (a) Leggio, A.; Liguori, A.; Procopio, A.; Sindona, G. Convenient and stereospecific homologation of N-fluorenylmethyloxycarbonyl-α-amino acids to their β-homologues J. Chem. Soc., Perkin Trans. 1 1997, 1969-1971;
12. (b) Muffler, A.; Vogt, C.; Sewald, N. Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted Wolff rearrangement. Synthesis 1998, 837-841;
13. (c) Winum, J.-Y.; Karnal, M.; Leydet, A.; Roque, J.-P.; Montero, J.-L. Homologation of carboxylic acids by Arndt-Eistert reaction under ultrasonic waves. Tetrahedron Lett. 1996, 37, 1781-1782.
14. (a) Paul, B. S.; Vasanthakumar, G.-R.; Suresh Babu, V. V. Microwave-assisted Wolff rearrangement: A facile method for the synthesis of Fmoc-β-amino acids. Lett. Pept. Sci. 2002, 9, 231-233;
15. (b) Sudrik, S. G.; Chavan, S. P.; Chandrakumar, K. R. S.; Pal, S.; Date, S. K.; Chavan, S. P.; Sonawane, H. R. Microwave specific Wolff rearrangement of α-diazoketones and its relevance to the nonthermal and thermal effect. J. Org. Chem. 2002, 67, 1574-1579.
16. Podlech, J.; Seebach, D. On the preparation of β-amino acids from α-amino acids using the Arndt-Eistert reaction: Scope, limitations and stereoselectivity. Application to carbohydrate peptidation. Stereoselective a-alkylations of some β-amino acids. Liebigs Ann. 1995, 1217-1228.
17. Patil, B. S.; Vasanthakumar, G.-R.; Suresh Babu, V. V. Synthesis of β-amino acids: 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) for activation of Fmoc-/Boc-/Z-α-amino acids. Synth. Commun. 2003, 33, 3089-3096.
18. Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. A general method for the synthesis of enantiomerically pure β-substituted, β-amino acids through α-substituted succinic acid derivatives. J. Org. Chem. 1999, 64, 6411-6417.
19. Kuwata, S.; Nakanishi, A.; Yamada, T.; Miyazawa, T. Total synthesis of leucinostatin D. Tetrahedron Lett. 1992, 33, 6995-6998.
20. Guibourdenche, C.; Seebach, D.; Natt, F. Use of the Wolff rearrangement of diazo ketones from amino acids as a synthetic method for the formation of oligonucleopeptides: A novel approach to chimeric biomolecules. Helv. Chim. Acta. 1997, 80, 1-13.