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Description
One of the oldest methods in electroorganic synthesis is Kolbe reaction, where alkyl radical is generated upon anodic decarboxylation. In contrast, Hofer-Moest reaction provides a carbocation after anodic decarboxylation followed by a reaction with a nucleophile.
Aminomalonic acid derivatives are readily available substrates that can be relatively easily functionalized, e.g. by alkylation reactions. Herein we report a previously unreported intramolecular Hofer-Moest reaction of N-substituted 2-aminomalonic acid monoesters. A stabilized cation 2 is formed after anodic decarboxylation of a malonic acid monoester 1 followed by intramolecular cyclization. The developed method allows to obtain new tetrahydrofurane and tetrahydropyrane fragment containing amino acid derivatives 3 in good yields.
