Chiral building blocks: enantioselective syntheses of benzyloxymethyl phenyl propionic acids

Molecules. 2004 May 31;9(6):449-58. doi: 10.3390/90600449.

Abstract

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.

MeSH terms

  • Alkylation
  • Models, Chemical
  • Molecular Structure
  • Propionates / chemical synthesis*
  • Propionates / chemistry*
  • Stereoisomerism
  • Titanium / chemistry

Substances

  • Propionates
  • titanium tetrachloride
  • Titanium
  • propionic acid