The extremely useful chiral building blocks 3-hydroxy-2-alkylpropionat
es 8 are prepared in either S or R enantiomeric form via the diastereo
selective addition of chiral alcohols to arylketenes 4 and the manipul
ation of the resultant chiral 2-arylaliphatic esters 5 and 6. Applicat
ion of this methodology to the asymmetric syntheses of 3-mercapto-2-al
kylpropionates (9) and (S)-(-)-paraconic acid (3) is described.