Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

Molecules

Jack G. Parsons¹  Danuta Stachurska-Buczek¹  Neil Choi¹  Peter G. Griffiths¹  Daniel A. Huggins¹  Beata M. Krywult¹  Sharon T. Marino¹  Thao Nguyen¹  Craig S. Sheehan¹  Ian W. James¹  Andrew M. Bray¹  Jonathan M. White² 

[1] Mimotopes Pty Ltd. 11 Duerdin Street, Clayton, Victoria 3168, Australia. Tel. [phone], Fax [phone].;School of Chemistry, University of Melbourne, Victoria 3010, Australia.

关键词: TiCl₄;    stereoselective;    alkylation;    benzyloxymethylphenylpropionic acids.;   

DOI  :  10.3390/90600449

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
2004 by MDPI (http://www.mdpi.org).