Conference Proceedings
Chiral building blocks: Enantioselective syntheses of benzyloxymethyl phenyl propionic acids
JG Parsons, D Stachurska-Buczek, N Choi, PG Griffiths, DA Huggins, BM Krywult, ST Marino, T Nguyen, CS Sheehan, IW James, AM Bray, JM White, RS Boyce
Molecules | MDPI | Published : 2004
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.