Soluble Polymer-Supported Synthesis of α-Amino Acid Derivatives

Synthetic Communications

Volumn 34, Issue 2, 2004, Pages 219-224

  Hu, Chunling ^a   Chen, Zuxing ^a   Yang, Guichun ^a  

^a HUBEI UNIVERSITY   (China)

Author keywords

Amino acid derivatives; LPOS; Soluble polymer support; SPOS; Synthesis

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; POLYMER;

AMINO ACID SYNTHESIS; ARTICLE; CATALYST SUPPORT; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LIQUID; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRECIPITATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; SUBSTITUTION REACTION; TECHNIQUE; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

EID: 1342280484     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120027256     Document Type: Article

References (17)

1. (a) Boto, A.; Hernandez, R.; Montoya, A. One-pot synthesis of aryl glycines and other unnatural amino acids from serine derivatives. Tetrahedron Lett. 2002, 43, 8269;
2. (b) Reichwein, J.; Liskamp, R. Site-specific N-alkylation of peptides on the solid phase. Tetrahedron Lett. 1998, 39, 1243;
3. (c) Spengler, J.; Burger, K. An efficient synthesis of N-methylamino acids and some of their derivatives. Synthesis 1998, 67;
4. (d) Reddy, G.V.; Rao, G.V.; Iyengar, D.S. A practical approach for the optically pure N-methyl-α-amino acids. Tetrahedron Lett. 1998, 39, 1985.
5. Humphrey, J.M.; Chamberlin, A.R. Chemical synthesis of natural products: coupling methods for the incorporation of noncoded amino acids into peptides. Chem. Rev. 1997, 97, 2243.
6. (a) Beck, G. Synthesis of chiral drug substances. Synlett. 2002, 837;
7. (b) Berkowitz, D.B.; Chisowa, E. Stereo-phase synthesis of quaternary β-γ-unsaturated amino acids: chain extension of d- and 1- α-(2-tributylstannyl)vinyl amino acids. Tetrahedron 2001, 57, 6329.
8. (a) Lloyd-Joned, G.C. Palladium-catalyzed α-arylation of esters: ideal new methodology for discovery chemistry. Angew. Chem. Int. Ed. 2002, 41, 953;
9. 4-promoted Friedel-Crafts reaction of phenols with chiral N,O-hemiacetal. Synlett. 2002, 37;
10. 2 in the presence of TmSCl leading to indolyl primary amines. Tetrahedron Lett. 2002, 43, 4821;
11. (d) Janczuk, A.; Zhang, W.; Xie, W.; Lou, S.; Cheng, J.-P.; Wang, P.G. Ytterbium triflate catalyzed electrophilic substitution of indoles: the synthesis of unnatural tryptophan derivatives. Tetrahedron Lett. 2002, 43, 4271.
12. O'Donnell, M.J.; Delgado, F.; Drew, M.D. Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent. Tetrahedron Lett. 1999, 40, 5831.
13. Parrick, H.Y.; Kim, D.J. Soluble polymer-supported organic synthesis. Acc. Chem. Res. 2002, 33, 546.
14. (a) Yang, G.C.; Chen, Z.X.; Zhang, Z.J. Novel synthesis of monoethers of hydroquinone and resorcinol on soluble polymer-supports. Synth. Commun. 2002, 32, 3637;
15. (b) Yang, G.C.; Chen, Z.X.; Zhang, Z.J. Synthesis of thiourea derivatives on soluble polymeric support. Chin. J. Chem. 2002, 20, 178;
16. (c) Chen, Z.X.; Yang, G.C.; Zhang, Z.J. Synthesis of a library of N-p-hydroxybenzoyl thioureas using a poly(ethylene glycol) support. Synthesis 2001, 1483.
17. Luo, Y.; Ouyang, X.H.; Robert, W.A.; Murphy, M.M. A case study of employing spectroscopic tools for monitoring reactions in the developmental stage of a combinatorial chemistry library. J. Org. Chem. 1998, 63, 8719.