Next Article in Journal
Next Article in Special Issue
Previous Article in Journal
Previous Article in Special Issue
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)
Download PDF [203 KB, uploaded 18 June 2014]
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.

Export to BibTeX |
EndNote


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.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert