Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

Autor: Rustum S. Boyce, Jonathan M. White, Andrew M. Bray, Ian W. James, Craig S. Sheehan, Thao Nguyen, Sharon T. Marino, Beata M. Krywult, Daniel A. Huggins, Peter G. Griffiths, Neil Choi, Danuta Stachurska-Buczek, Jack G. Parsons
Jazyk: angličtina
Rok vydání: 2004
Předmět:
Zdroj: Molecules, Vol 9, Iss 6, Pp 449-458 (2004)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/90600449
Popis: 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.
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