Use of diphenyliodonium bromide in the synthesis of some N-phenyl-amino acids

Synthetic Communications

Volumn 40, Issue 8, 2010, Pages 1161-1179

  McKerrow, Jason D ^a   Al Rawi, Jasim M A ^a   Brooks, Peter ^b  

^a LA TROBE UNIVERSITY   (Australia)

^b UNIVERSITY OF THE SUNSHINE COAST   (Australia)

Author keywords

Amino acids; Diphenyliodonium bromide; Esters; N phenylation

Indexed keywords

ASPARTIC ACID; DIPEPTIDE; DIPHENYLIODONIUM SALT; ESTER; GLUTAMIC ACID; ISOLEUCINE; PHENYLALANINE; PROLINE; SERINE; SILVER NITRATE; THREONINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICROANALYSIS; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77949394916     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903051259     Document Type: Article

References (30)

1. (a) Ma, D.; Yao, J. Synthesis of chiral N-aryl-a-amino acids by Pd Cu catalysed couplings of chiral a-amino acids with aryl halide. Tetrahedron: Asymmetry 1996, 7, 3075-3078;
2. (b) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. Accelerating effect induced by the structure of R-amino acid in the copper-catalyzed coupling reaction of aryl halides with R-amino acids: Synthesis of benzolactam-V8. J. Am. Chem. Soc. 1998, 120, 12459-12467;
3. (c) Johnston, A. D.; Asmussen, E.; Bowen, R. L. Substitutes for N-phenylglycine in adhesive bonding to dentin. J. Dent. Res. 1989, 68, 1337-1344;
4. (d) Chen, R. S.; Bowen, R. L. The use of N-phenylglycine in a dental adhesive system. J. Adhes. Sci. Technol. 1989, 3, 49-54;
5. (e) Farahani, M.; Antonucci, J. M.; Phinney, C. S.; Karam, L. S. Mass spectrometric analysis of polymers derived from N-aryl-a-amino acid initiators. J. Appl. Polym. Sci. 1997, 65, 561-565;
6. (f) Bader, M.; Lehnert, G.; Angerer, J. GC=MS determination of N-phenylalanine, a possible biomarker for benzene exposure in human haemoglobin by the N-alkyl-Edman method. Int. Arch. Occup. Environ. Health 1994, 65, 411-414;
7. (g) Rottger, S., Sjoberg, P. J. R.; Larhed, M. Microwave-enhanced copper-catalyzed N-arylation of free and protected amino acids in water. J. Comb. Chem. 2007, 9, 204-209;
8. (h) Jiang, Q.; Jiang, D.; Jiang, Y.; Fu, H.; Zhao, Y. A mild and efficient method for copper-catalyzed Ullmann-type N-arylation of aliphatic amines and amino acids. Synlett 2007, 12, 1836-1842;
9. (i) Kurokawa, M.; Nakanishi, W.; Ishikawa, T. Copper (I) iodide-catalyzed coupling reaction of haloindoles with a-amino acids. Heterocycles 2007, 71(4), 847-854;
10. (j) Bachmann, S.; Fielenbach, D.; Jørgensen, K. A. Cu(I)-carbenoid-and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of a diazo compounds into N-H bonds. Org. Biomol. Chem. 2004, 2, 30444-33049;
11. (k) Liu, B.; Zhu, S.-F.; Zhang, W.; Chen, C.; Zhou, Q.-L. Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral spiro bisoxazolines. J. Am. Chem. Soc. 2007, 129, 5834-5835.
12. Quick, J.; Saha, B.; Driedger, P. E. Protein kinase C modulators, indolactams, 1: Efficient and flexible routes for the preparation of (-)-Indolactam V for use in the synthesis of analogs. Tetrahedron Lett. 1994, 35, 8549-8552.
13. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams: A clarification of the conformational flexibility problem in structure-activity studies of teleocidins. J. Am. Chem. Soc. 1996, 118, 1841-1855.
14. (a) Klebe, J. F.; Finkbeiner, H. Optically active silicon in 2-siloxazolidones-5: An asymmetric synthesis. J. Am. Chem. Soc. 1968, 90, 7255-7261;
15. (b) Portoghese, P. S. Stereochemical studies on medicina1 agents, II: Absolute configuration of (-)-phenampro-mide. J. Med. Chem. 1965, 8, 147-150;
16. (c) Takeda, A. Synthesis of ring-substituted N-phenylglycines, their nitriles and amides. J. Org. Chem. 1957, 22, 1096-1100.
17. Beringer, F. M.; Brierly, A.; Drexler, M.; Gindler, E. M.; Lumpkin, C. C. Diaryliodonium salts, II: The phenylation of organic and inorganic bases. J. Am. Chem. Soc. 1953, 75, 2708-2712.
18. Sigma-Aldrich, http://www.sigmaaldrich.com/catalog, glycine methyl ester hydro-chloride [Aldrich G6600], L-alanine methyl ester hydrochloride [Aldrich 330639], L-valine methyl ester hydrochloride [Aldrich 860271], L-leucine methyl ester hydrochloride [Aldrich L1002], L-isoleucine methyl ester hydrochloride [Fluka 58920], L-phenylalanine methyl ester hydrochloride [Aldrich P17202], L-methionine methyl ester hydrochloride [Aldrich 860409], L-proline methyl ester hydrochloride [Aldrich 287067], L-serine methyl ester hydrochloride [Aldrich 412201], L-threonine methyl ester hydrochloride [Fluka 89210], L-tyrosine methyl ester hydrochloride [Aldrich 850489], L-aspartic acid dimethyl ester hydrochloride [Aldrich 456233], L-glutamic acid diethyl ester hydrochloride [Aldrich 309346](a)
19. (b) Baumgarten, H. E.; Dirks, J. E.; Petersen, J. M.; Zey, R. L. Reactions of amines, XV: Synthesis of a-amino acids from imino esters. J. Org. Chem. 1966, 31, 3708-3711;
20. (c) Chambers, R. W.; Carpenter, F. H. The preparation and properties of some amino acid amides. J. Am. Chem. Soc. 1955, 77, 1522-1526.
21. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1994.
22. Devedjiev, I. T. Synthesis of esters and peptides of natural amino acids. Bulg. Chem. Commun. 2006, 38, 7-13.
23. 1H chemical shift non-equivalence of several a-amino ester signals using tris[3-(trifluoromethylhydroxy-methylene)-(\+)-camphorato]samarium(III): a chiral lanthanide shift reagent that causes minimal line broadening. Tetrahedron: Asymmetry 2004, 15, 2351-2356.
24. Narumi, F.; Hattori, T.; Matsumura, N.; Onodera, T.; Katagiri, H.; Kabuto, C.; Kameyama, H.; Miyano, S. Synthesis of an inherently chiral O,O-bridged thiacalix[4]-crowncarboxylic acid and its application to a chiral solvating agent. Tetrahedron 2004, 60, 7827-7833.
25. Yamada, T.; Lukac, P. J.; Yu, T.; Weiss, R. G. Reversible, room-temperature, chiral ionic liquids: Amidinium carbamates derived from amidines and amino-acid esters with carbon dioxide. Chem. Mater. 2007, 19, 4761-4768.
26. Roettger, S.; Sjoberg Per, J. R.; Larhed, M. Microwave-enhanced copper-catalyzed N-arylation of free and protected amino acids in water. J. Comb. Chem. 2007, 9, 204-209.
27. Sigma-Aldrich http://www.sigmaaldrich.com/catalog, L-tyrosine methyl ester [Aldrich T90808].
28. Clement, J.-B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synthesis of SB-214857 using copper catalyzed amination of aryl bromides with L-aspartic acid. Synlett 2001, 1423-1427.
29. Henkel, B.; Weber, L. A novel four-component synthesis of N-substituted amino acid esters. Synlett 2002, 1877-1879.
30. Gately, D. A.; Norton, J. R. Origin of stereochemistry in the R-amino acid esters and amides generated from optically active zirconaaziridine complexes. J. Am. Chem. Soc. 1996, 118, 3479-3489.