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

Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

Jack G. Parsons 1, Danuta Stachurska-Buczek 1, Neil Choi 1, Peter G. Griffiths 1, Daniel A. Huggins 1, Beata M. Krywult 1, Sharon T. Marino 1, Thao Nguyen 1, Craig S. Sheehan 1, Ian W. James 1, Andrew M. Bray 1,* email, Jonathan M. White 2 and Rustum S. Boyce 3
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.
Keywords: TiCl4; stereoselective; alkylation; benzyloxymethylphenylpropionic acids.

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Cite This Article

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.

AMA 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(6):449-458.

Chicago/Turabian Style

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. 2004. "Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids." Molecules 9, no. 6: 449-458.

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