Molecules 2004-01-01

Chiral building blocks: enantioselective syntheses of benzyloxymethyl phenyl propionic acids.

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

Index: Molecules 9(6) , 449-58, (2004)

Full Text: HTML

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.