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Direct Reductive Amination of Biobased Furans to <i>N</i>‐Substituted Furfurylamines by Engineered Reductive Aminase

Ziyue Yang, Yacheng Hao, Song‐Qing Hu, Min‐Hua Zong, Qi Chen, Ning Li

2021Advanced Synthesis & Catalysis26 citationsDOI

Abstract

Abstract Furfurylamines are important building blocks for the synthesis of many pharmacologically active compounds and polymers. In this work, direct reductive amination of biobased furans to N ‐substituted furfurylamines by reductive aminase from Aspergillus oryzae ( Asp RedAm) was reported. Besides the reductive aminase activity, Asp RedAm also showed a promiscuous, yet low alcohol dehydrogenase activity. The variant W210F proved to be a good catalyst for the synthesis of N ‐substituted furfurylamines. Furans were transformed to the target products with the conversions up to &gt;99% and selectivities up to &gt;99%. In addition, N ‐substituted furfurylamines were synthesized in the total turnover number (TTN) up to 3200 on a preparative scale, indicating the applicability of this biocatalytic route in synthetic chemistry. magnified image

Topics & Concepts

Reductive aminationChemistryCatalysisOrganic chemistryReductive eliminationCombinatorial chemistryAminationAlcohol dehydrogenaseAlcoholCatalysis for Biomass ConversionAsymmetric Hydrogenation and Catalysis
Direct Reductive Amination of Biobased Furans to <i>N</i>‐Substituted Furfurylamines by Engineered Reductive Aminase | Litcius