A New Synthesis of p-Hydroxy Phenylglycine and Some Analogues from p-Benzoquinone
- 1 February 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (4) , 473-475
- https://doi.org/10.1021/ol9913183
Abstract
[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.Keywords
This publication has 2 references indexed in Scilit:
- Synthesis of DL‐2‐(p‐hydroxyphenyl)glycine by the ammonolysis of p‐hydroxymandelic acid obtained by the condensation of phenol with glyoxylic acidJournal of Chemical Technology & Biotechnology, 1989
- Addition of functionalized organolithium reagents to p-benzoquinones and cyclohexadienones: synthesis of functionalized cyclohexadienones, dienols and dienediolsTetrahedron Letters, 1983