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Updated: Jul 10, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization
Julie Gratien1, Marie-Pierre Heck, Charles Mioskowski
1CEA, DSV, iBiTecS, Service de Chimie Bioorganique et de Marquage (SCBM), Bât 547, Gif sur Yvette F-91191, France.
Abstract:
The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-d-gluconolactone or 2,3,4,6-tetra-O-benzyl-d-mannonolactone with MgI(2) in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction.
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