Chiral building blocks: enantioselective syntheses of benzyloxymethyl phenyl propionic acids

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-...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2004-05, Vol.9 (6), p.449-458
Main Authors: 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
Format: Article
Language:English
Subjects:
Acids
Alkylation
benzyloxymethylphenylpropionic acids
Crystal structure
Hydrogenation
Models, Chemical
Molecular Structure
Pharmaceutical industry
Propionates - chemical synthesis
Propionates - chemistry
Reagents
Stereoisomerism
stereoselective
TiCl4
Titanium - chemistry
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/90600449