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Molecules 2004, 9(6), 449-458; doi:10.3390/90600449
Article

Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

1, 1, 1, 1, 1, 1, 1, 1, 1, 1, 1,* , 2 and 3
Received: 14 May 2004 / Accepted: 27 May 2004 / Published: 31 May 2004
(This article belongs to the Special Issue RACI 2003 symposium)
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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.
Keywords: TiCl4; stereoselective; alkylation; benzyloxymethylphenylpropionic acids. TiCl4; stereoselective; alkylation; benzyloxymethylphenylpropionic acids.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Parsons, J.G.; Stachurska-Buczek, D.; Choi, N.; Griffiths, P.G.; Huggins, D.A.; Krywult, B.M.; Marino, S.T.; Nguyen, T.; Sheehan, C.S.; James, I.W.; Bray, A.M.; White, J.M.; Boyce, R.S. Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids. Molecules 2004, 9, 449-458.

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