Abstract
Nucleophilic displacement reactions, by thioacetate, thiobenzoate, methanethiolate, and toluene-α-thiolate, on methyl L-O-ptolysulphonyl-lactate, methyl L-2-chloropropionate, and sodium L-2-chloropropionate, have been used to prepare D-2-acylthio- and D-2-acylthio- and D-2-alkylthio-propionic acids and esters. Extensive racemisation occurs when an excess of thioacetate or thiobenzoate is used; this is attributed to further SN2 displacement, with acetylthio or benzoylthio as a leaving group. Concomitant acyl exchange also occurs, with retention of configuration, by a different mechanism. Thus methyl D-2-acetylthiopropionate with potassium thiobenzoate gives methyl D-2-benzoylthiopropionate.
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