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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 8
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Original Articles

Use of Diphenyliodonium Bromide in the Synthesis of Some N-Phenyl α-Amino Acids

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Pages 1161-1179 | Received 30 Jan 2009, Published online: 12 Mar 2010

REFERENCES

  • (a) Ma , D. ; Yao , J. Synthesis of chiral N-aryl-α-amino acids by Pd Cu catalysed couplings of chiral α-amino acids with aryl halide . Tetrahedron: Asymmetry 1996 , 7 , 3075 – 3078 ; (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 ; (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 ; (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 ; (e) Farahani , M. ; Antonucci , J. M. ; Phinney , C. S. ; Karam , L. S. Mass spectrometric analysis of polymers derived from N-aryl-α-amino acid initiators . J. Appl. Polym. Sci. 1997 , 65 , 561 – 565 ; (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 ; (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 ; (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 ; (i) Kurokawa , M. ; Nakanishi , W. ; Ishikawa , T. Copper (I) iodide-catalyzed coupling reaction of haloindoles with α-amino acids . Heterocycles 2007 , 71 ( 4 ), 847 – 854 ; (j) Bachmann , S. ; Fielenbach , D. ; J⊘rgensen , 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 – 3049 ; (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 .
  • 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 .
  • 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 .
  • (a) Klebe , J. F. ; Finkbeiner , H. Optically active silicon in 2-siloxazolidones-5: An asymmetric synthesis . J. Am. Chem. Soc. 1968 , 90 , 7255 – 7261 ; (b) Portoghese , P. S. Stereochemical studies on medicina1 agents, II: Absolute configuration of (–)-phenampromide . J. Med. Chem. 1965 , 8 , 147 – 150 ; (c) Takeda , A. Synthesis of ring-substituted N-phenylglycines, their nitriles and amides . J. Org. Chem. 1957 , 22 , 1096 – 1100 .
  • 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 .
  • (a) Sigma-Aldrich, http://www.sigmaaldrich.com/catalog, glycine methyl ester hydrochloride [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] (b) Baumgarten , H. E. ; Dirks , J. E. ; Petersen , J. M. ; Zey , R. L. Reactions of amines, XV: Synthesis of α-amino acids from imino esters. J. Org. Chem. 1966, 31, 3708–3711; (c) Chambers , R. W. ; Carpenter , F. H. The preparation and properties of some amino acid amides. J. Am. Chem. Soc. 1955, 77, 1522–1526.
  • Bodanszky , M. ; Bodanszky , A. The Practice of Peptide Synthesis, , 2nd ed. ; Springer-Verlag : Berlin , 1994 .
  • Devedjiev , I. T. Synthesis of esters and peptides of natural amino acids . Bulg. Chem. Commun. 2006 , 38 , 7 – 13 .
  • Omata , K. ; Aoyagi , S. ; Kabuto , K. Observing the enantiomeric 1H chemical shift non-equivalence of several α-amino ester signals using tris[3-(trifluoromethylhydroxymethylene)-(+)-camphorato]samarium(III): a chiral lanthanide shift reagent that causes minimal line broadening . Tetrahedron: Asymmetry 2004 , 15 , 2351 – 2356 .
  • 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 .
  • 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 .
  • 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 .
  • Sigma-Aldrich, http://www.sigmaaldrich.com/catalog, L-tyrosine methyl ester [Aldrich T90808] .
  • 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 .
  • Henkel , B. ; Weber , L. A novel four-component synthesis of N-substituted amino acid esters . Synlett 2002 , 1877 – 1879 .
  • 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 .

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