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

Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

1
Mimotopes Pty Ltd. 11 Duerdin Street, Clayton, Victoria 3168, Australia
2
School of Chemistry, University of Melbourne, Victoria 3010, Australia
3
Chiron Corporation, 4560 Horton St, Emeryville, California 94608, USA
*
Author to whom correspondence should be addressed.
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. View Full-Text
Keywords: TiCl4; stereoselective; alkylation; benzyloxymethylphenylpropionic acids. TiCl4; stereoselective; alkylation; benzyloxymethylphenylpropionic acids.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

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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