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Yttrium-Catalyzed Regioselective Aminolysis of 2,3-Epoxy Esters and Amides

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Herein a yttrium-catalyzed regioselective ring opening reaction of 2,3-epoxy esters and amides with amines as nucleophiles is pre-sented. This method features high regiocontrol, enantiospecific SN2 reaction pathway, broad substrate scope… Click to show full abstract

Herein a yttrium-catalyzed regioselective ring opening reaction of 2,3-epoxy esters and amides with amines as nucleophiles is pre-sented. This method features high regiocontrol, enantiospecific SN2 reaction pathway, broad substrate scope and mild reaction condi-tions, furnishing a wide range of α-hydroxyl β-amino esters and amides in regioisomerically pure form. Notably, the selective nucle-ophilic attack to the C-3 position is controlled by the directing effect of the carbonyl group of the substrates.

Keywords: epoxy esters; catalyzed regioselective; yttrium catalyzed; esters amides

Journal Title: Synlett
Year Published: 2023

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