A new synthesis of p-hydroxy phenylglycine and some analogues from p-benzoquinone
[reaction: see text] 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.
Titulaer
GT
Department of Organic Chemistry, NSR Institute for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld, The Netherlands.
Zhu
J
Klunder
AJ
Zwanenburg
B