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Synlett 1998; 1998(4): 363-364
DOI: 10.1055/s-1998-1662
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Synthesis of (R)-Aryloxy Acids by SN2 Reaction from Diastereomerically Enriched α-Bromo Esters

Rosa Amoroso* , Giancarlo Bettoni, Maria Luisa Tricca
  • *Istituto di Scienze del Farmaco, Università "G. D'annunzio", Via dei Vestini, Chieti 66100, Italy; Fax 0871/3 55 67 78; E-mail: bettoni@unich.it
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Publikationsdatum:
31. Dezember 2000 (online)

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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