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Electrochemical Synthesis of a Sitagliptin Precursor.

Elisabeth K OehlPaul T JirschJasmin HammesAndreas StengleinMaría MéndezSven RufSiegfried R Waldvogel
Published in: The Journal of organic chemistry (2024)
A novel synthesis of sitagliptin based on a redox-active ester derived from the chiral pool is reported. The key step is an electrochemical nickel-catalyzed sp 2 -sp 3 cross-coupling reaction using inexpensive nickel foam in an undivided cell. It was successfully applied to 21 examples in up to 88% yield. These sitagliptin-analogue precursors could potentially interact with the DPP4 enzyme. A full synthesis based on our new reaction pathway provided sitagliptin in an overall yield of 33%.
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