SYNTHESIS OF NONPROTEINOGENIC AMINO ACIDS PART 2: PREPARATION OF A SYNTHETIC EQUIVALENT OF THE γ-ANION SYNTHON FOR ASYMMETRIC AMINO ACID SYNTHESIS

Article abstract of DOI:10.1016/0040-4020(89)80144-9

The synthesis of α-t-butyl γ-methyl N-trityl-(S)-glutamate (12) from (S)-glutamic acid (6) is described.Diester (12), on treatment with lithium isopropylcyclohexylamide followed by the addition of carbonyl compounds, reacts to give the γ-substituted glutamic acid derivatives (13a-i) with retention of optical purity at the α centre.