Stereolibrary of spirocyclic building blocks

What is it about?

This manuscript reports on the synthesis of a library of stereoisomeric 1-aminospiro[3.3]heptane-1,6-dicarboxylic acids. An original synthetic scheme allowing constructing the molecular scaffold of the target molecules and separating the stereoisomers was elaborated. Interestingly, stable oxaphosphetanes (usually fleeting intermediates of the Wittig reaction) were detected along the synthesis.

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Why is it important?

The synthesized compounds are restricted analogues of the glutamic acid, so they might be used in mechanistic study of enzymes and receptors which act on glutamate. The described approach may also find use in synthesis of drug-like libraries of the spiro[3.3]heptane derivatives.