A NOVEL APPLICATION OF THE CHIRAL REAGENT (S)-2-N-(N'-BENZYLPROLYL)-AMINOBENZALDEHYDE: SYNTHESIS OF OPTICALLY PURE α-METHYLVALINE AND α-METHYLGLUTAMIC ACID

Article abstract of DOI:10.1007/BF00961232

The synthesis of α-methyl substituted amino acids using Ni(II) complexes of the Schiff base obtained from alanine and (S)-2-N-(N'-benzylpropyl)aminobenzaldehyde is described.This complex was alkylated with isopropyl bromide, gramine iodomethylate, and methyl acrylate (in a Michael reaction).From the resulting mixtures of products, diastereomerically pure complexes were obtained by crystallization or silica gel chromatography.Both (S)- and (R)-enantiomers of the optically active amino acids α-Me-Val and α-MeGlu were obtained after decomposing the diastereomerically pure complexes.