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Cesium Carbonate Catalyzed Esterification of N-Benzyl-N-Boc-amides under Ambient Conditions.

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We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst.… Click to show full abstract

We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst. This method exhibits broad substrate scope and represents a practical alternative to existing esterification strategies. The synthetic utility of this protocol is demonstrated via the facile synthesis of crown ether derivatives and the late-stage modification of a representative natural product and several sugars in reasonable yields.

Keywords: cesium carbonate; benzyl boc; esterification; carbonate catalyzed; catalyzed esterification; esterification benzyl

Journal Title: Organic letters
Year Published: 2019

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