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 JG, Stachurska-Buczek D, Choi N, Griffiths PG, Huggins DA, Krywult BM, Marino ST, Nguyen T, Sheehan CS, James IW, Bray AM, White JM, Boyce RS. 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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