A Highly Diastereoselective Synthesis of 4-Alkyl Threo Glutamic Acids

Article abstract of DOI:10.1016/0957-4166(95)00274-S

Treatment of N-p-nitrobenzoyl L- or D-glutamic acid diester with lithium bis(trimethylsilyl)amide generates a chelated γ-enolate which reacts with alkyl halides to give (2S,4S)- or (2R,4R)-4-alkylated glutamic acid derivatives with very high diastereoselectivity.