CAS: 96406-06-3

3-(3-Chlorophenyl)-2-oxopropanoic acid is a diastereomer of 2-phenylpropanoic acid. It is used in the synthesis of diketopiperazines, which are analogues of amphetamines. The synthesis proceeds by the addition of ethyl chloroacetate to α-chloroacrylic acid followed by reaction with cyclohexanol and then reduction with lithium aluminum hydride. The stereoselectivity of this reaction is determined by the enantioselective transfer of a proton from the hydroxyl group to the adjacent carbonyl group. This process occurs more readily when an enantiomerically pure chiral catalyst is used, leading to a diastereoselective synthesis.