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