ALPHA-HYDROXYMETHYLPHENYLGLYCINE AND ALPHA-HYDROXYMETHYLPHENYLALANINE- SYNTHESIS, RESOLUTION, AND ABSOLUTE-CONFIGURATION

Racemic alpha-hydroxymethylphenylglycine and alpha-hydroxymethylypheny lalanine have been synthesized by selective hydroxymethylation of oxaz olones derived from phenylglycine and phenylalanine, and resolved into enantiomers by fractional crystallization of their diastereoizomeric salts with (-)-cynchonidine or (-)-quinine, respectively. The absolute configuration of laevorotatory alpha-hydroxymethylphenylglycine has b een elucidated to be (S) by the chemical correlation with (R)-alpha-me thylphenylglycine. The absolute configuration of dextrorotatory alpha- hydroxymethylphenylalanine has been proved to be (S) by tile chemical correlation with (R)-alpha-methylphenylalanine.