Chemo-enzymatic synthesis of pyrazines and pyrroles

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Abstract

Herein we report the biocatalytic synthesis of substituted pyrazines and pyrroles using a transaminase to mediate the key amination of the ketone precursors. Treatment of α‐diketones with ATA‐113 in the presence of a suitable amine donor yielded the corresponding α‐amino ketones which underwent oxidative dimerization to the pyrazines. Selective amination of α‐diketones in the presence of β‐keto esters afforded substituted pyrroles in a biocatalytic equivalent of the classical Knorr pyrrole synthesis. Finally we have shown that pyrroles can be prepared by internal amine transfer catalyzed by a transaminase in which no external amine donor is required.

Bibliographical metadata

Original languageEnglish
JournalAngewandte Chemie International Edition
Early online date18 Oct 2018
DOIs
Publication statusPublished - 2018

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