title: Chiral building blocks: enantioselective syntheses of benzyloxymethyl phenyl propionic acids.
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.
authors.affiliation: Mimotopes Pty Ltd. 11 Duerdin Street, Clayton, Victoria 3168, Australia.
authors.forename: Jack G
authors.initials: JG
authors.lastname: Parsons
authors.forename: Danuta
authors.initials: D
authors.lastname: Stachurska-Buczek
authors.forename: Neil
authors.initials: N
authors.lastname: Choi
authors.forename: Peter G
authors.initials: PG
authors.lastname: Griffiths
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Huggins
authors.forename: Beata M
authors.initials: BM
authors.lastname: Krywult
authors.forename: Sharon T
authors.initials: ST
authors.lastname: Marino
authors.forename: Thao
authors.initials: T
authors.lastname: Nguyen
authors.forename: Craig S
authors.initials: CS
authors.lastname: Sheehan
authors.forename: Ian W
authors.initials: IW
authors.lastname: James
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Bray
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.forename: Rustum S
authors.initials: RS
authors.lastname: Boyce
mesh_terms: D000478:Alkylation; D008956:Models, Chemical; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
chemical_list: D011422:Propionates; C025096:titanium tetrachloride; D014025:Titanium; C029658:propionic acid