SYNTHESIS OF (R)-ARYLOXY ACIDS BY S(N)2 REACTION FROM DIASTEREOMERICALLY ENRICHED ALPHA-BROMO ESTERS

Authors
AMOROSO R BETTONI G TRICCA ML
Citation
R. Amoroso et al., SYNTHESIS OF (R)-ARYLOXY ACIDS BY S(N)2 REACTION FROM DIASTEREOMERICALLY ENRICHED ALPHA-BROMO ESTERS, Synlett, (4), 1998, pp. 363
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
4
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):4<363:SO(ABS>2.0.ZU;2-D
Abstract
The S(N)2 reaction between diastereomerically enriched (R)-pantolacton e (S)-alpha-bromoesters and sodium p-chloroaryloxide affords chiral ar yloxy esters. Depending on the solvent used in the reaction, the diast ereomeric ratios could be strongly modified or inverted. In DMSO, the epimerization can be prevented and the (R)-aryloxy esters are obtained with good diastereomeric ratios.