Chiral building blocks: enantioselective syntheses of benzyloxymethyl phenyl propionic acids |
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| 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 |
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| Institution: | Mimotopes Pty Ltd. 11 Duerdin Street, Clayton, Victoria 3168, Australia. |
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| 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. |
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