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The primary Dieckmann cyclization product of the methyl (3,6-dioxopiperazin-2-yl)propionate was trapped with chlorotrimethylsilane and recrystallized. The X-ray crystal structure analysis showed (S)-configuration of the novel chiral centre. This configuration supports the hypothesis that formation of the stable lithium chelate is responsible for shifting this unusual Dieckmann cyclization towards the bicyclic product.

Stereoselectivity during a Dieckmann Analogous Cyclization of (Piperazin-2-yl)propionic Acid Esters