Studies of 2-Substituted 1,3-Oxazolidin-5-ones and 1,3-Oxazinan-6-ones as Precursors for the Synthesis of N-Alkyl-β-Amino Acids

REFERENCES

• Goodfellow , V. S. ; Marathe , M. V. ; Kuhlman , K. G. ; Fitzpatrick , T. D. ; Cuadrado , D. ; Hanson , W. ; Zuzack , J. S. ; Ross , S. E. ; Wieczoreck , M. ; Burkard , M. ; Whalley , E. T. Bradykinin receptor antagonists containing N-substituted amino acids: in vitro and in vivo B2 and B1 receptor antagonist activity . J. Med. Chem. 1996 , 39 , 1472 – 1484 .
   PubMedGoogle Scholar
• Aurelio , L. ; Hughes , A. B. Synthetic preparation of N-methyl-α-amino acids . Chem. Rev. 2004 , 104 , 5823 – 5846 .
   PubMed Web of Science ®Google Scholar
• Cheung , S. T. ; Benoiton , N. L. N-Methylamino acids in peptide synthesis, VII: Studies on the enantiomeric purity of N-methylamino acids prepared by various procedures . Can. J. Chem. 1977 , 55 , 916 – 921 .
   Google Scholar
• Aurelio , L. ; Box , J. S. ; Brownlee , R. T. C. ; Hughes , A. B. ; Sleebs , M. M. An efficient synthesis of N-methyl amino acids by way of intermediate 5-oxazolidinones . J. Org. Chem. 2003 , 68 , 2652 – 2667 .
   PubMed Web of Science ®Google Scholar
• Aurelio , L. ; Brownlee , R. T. C. ; Hughes , A. B. A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan . Org. Lett. 2002 , 4 , 3767 – 3769 .
   PubMedGoogle Scholar
• Aurelio , L. ; Brownlee , R. T. C. ; Hughes , A. B. ; Sleebs , B. E. The facile production of N-methyl amino acids via oxazolidinones . Aust. J. Chem. 2000 , 53 , 425 – 433 .
   Google Scholar
• Sleebs , B. E. ; Hughes , A. B. Effective methods for the synthesis of N-methyl β-amino acids from all 20 common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones . Helv. Chim. Acta 2006 , 89 , 2611 – 2637 .
   Google Scholar
• Sleebs , B. E. ; Hughes , A. B. Synthesis of new β-amino acids via 5-oxazolidinones and the Arndt–Eistert procedure . Aust. J. Chem. 2005 , 58 , 778 – 784 .
   Google Scholar
• Sleebs , B. E. ; Hughes , A. B. Diastereoselective synthesis of α-methyl and α-hydroxy-β-amino acids via 4-substituted-1,3-oxazinan-6-ones . J. Org. Chem. 2007 , 72 , 3340 – 3352 .
   PubMed Web of Science ®Google Scholar
• Hughes , A. B. ; Mackay , M. F. ; Sleebs , M. M. (2R,4S)-3-N-(Fluoren-9-ylmethoxycarbonyl)-4-methyl-2-nonyloxazolidin-5-one . Acta Cryst. Sect. E 2003 , E59 , o1079 – o1081 .
   Google Scholar
• Hiskey , R. G. ; Jung , J. M. Azomethine chemistry, II: Formation of peptides from oxazolidin-5-ones . J. Am. Chem. Soc. 1963 , 85 , 578 – 582 .
   Google Scholar
• Ben-Ishai , D. Reaction of acylamino acids with paraformaldehyde . J. Am. Chem. Soc. 1957 , 79 , 5736 – 5737 .
   Web of Science ®Google Scholar
• Freidinger , R. M. ; Hinkle , J. S. ; Perlow , D. S. ; Arison , B. H. Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones . J. Org. Chem. 1983 , 48 , 77 – 81 .
   Google Scholar
• See Ref. 6 and 7, and references therein .
   Google Scholar
• Perrin , D. D. ; Armarego , W. L. F. Purification Of Laboratory Chemicals; , 3rd ed.; Pergamon : Oxford , 1988.
   Google Scholar
• Altmann , E. ; Nebel , K. ; Mutter , M. Versatile stereoselective synthesis of completely protected trifunctional α-methylated α-amino acid starting from alanine . Helv. Chim. Acta 1991 , 74 , 800 – 806 .
   Google Scholar