859966-60-2Relevant articles and documents
Chiral building blocks: Enantioselective syntheses of benzyloxymethyl phenyl propionic acids
Parsons, Jack G.,Stachurska-Buczek, Danuta,Choi, Neil,Griffiths, Peter G.,Huggins, Daniel A.,Krywult, Beata M.,Marino, Sharon T.,Nguyen, Thao,Sheehan, Craig S.,James, Ian W.,Bray, Andrew M.,White, Jonathan M.,Boyce, Rustum S.
, p. 449 - 458 (2007/10/03)
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.