A New Synthesis of p-Hydroxy Phenylglycine and Some Analogues from p-Benzoquinone

A new route to p-hydroxy phenylglycine and N-substituted analogues has been developed starting from p-benzoquinone. 1,2-Addition of methyl lithioacetate to p-benzoquinone and subsequent quenching of the oxygen anion with methyl chloroformate, followed by an elimination−addition reaction with an appropriate amine, resulted in the desired amino acid derivatives. A diastereoselectivity of 60% was achieved using 8-phenylmenthyl acetate as the chiral auxiliary.