Molecules (May 2004)

Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

  • Rustum S. Boyce,
  • Jonathan M. White,
  • Andrew M. Bray,
  • Ian W. James,
  • Craig S. Sheehan,
  • Thao Nguyen,
  • Sharon T. Marino,
  • Beata M. Krywult,
  • Daniel A. Huggins,
  • Peter G. Griffiths,
  • Neil Choi,
  • Danuta Stachurska-Buczek,
  • Jack G. Parsons

DOI
https://doi.org/10.3390/90600449
Journal volume & issue
Vol. 9, no. 6
pp. 449 – 458

Abstract

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The synthesis of (2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)- propionic acid, (2S)-2-benzyloxymethyl-3-(2-fluoro-4-methylphenyl)propionic acid and (2S)-2-benzyl-oxymethyl-3-(2,4-dimethylphenyl)propionic acid has been achieved by TiCl4 mediated alkylation of the corresponding (4R)-4-benzyl-3-[3-(2-fluoro-4-methoxyphenyl-, 2-fluoro-4-methylphenyl-, 2,4- dimethylphenyl-)propionyl]-2-oxazolidinones, followed by hydrolysis of the chiral auxiliary. The stereochemistry of the alkylation reaction was confirmed by an X-ray crystal structure of (4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2- fluoro-4-methylphenyl)propionyl]-2-oxazolidinone.

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