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Synlett 1998; 1998(4): 363-364
DOI: 10.1055/s-1998-1662
DOI: 10.1055/s-1998-1662
letter
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Synthesis of (R)-Aryloxy Acids by SN2 Reaction from Diastereomerically Enriched α-Bromo Esters
Further Information
Publication History
Publication Date:
31 December 2000 (online)
The SN2 reaction between diastereomerically enriched (R)-pantolactone (S)-α-bromoesters and sodium p-chloroaryloxide affords chiral aryloxy esters. Depending on the solvent used in the reaction, the diastereomeric 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.
(R)-aryloxy acids - asymmetric addition - nucleophilic displacement - α-bromo esters - (R)-pantolactone