Asymmetric synthesis of phenylbis(glycines)

Article abstract of DOI:10.1016/S0040-4020(96)00344-4

(S,S)-α,α'-Diamino-1,4-and 1,3-benzenediacetic acids and N-Boc- and N- Fmoc-derivatives have been prepared by stereoselective syntheses. The chiral auxiliary (S)-4-benzyl-2-oxazolidinone formed bisimides with benzenediacetlyl dichlorides. The imides were lithiated at both α-sites to the carbonyl groups and azidated stereoselectively alpha to both carbonyl groups by trisyl azide to provide (S,S)-α,α'-diazidobenzenediacetic acid derivatives which were reduced to amines by Sn(II) choride or by hydrogenolysis over Pd.