One‐pot Synthesis of 4‐Aminocyclohexanol Isomers by Combining a Keto Reductase and an Amine Transaminase

Autor: Javier González-Sabín, Matthias Höhne, Kollipara Venkata Manideep, Sebastian Günther, Nicolás Ríos-Lombardía, Simon Merdivan, Francisco Morís, Olha Sviatenko, Philipp Süss
Rok vydání: 2019
Předmět:
Zdroj: ChemCatChem. 11:5794-5799
ISSN: 1867-3899
1867-3880
DOI: 10.1002/cctc.201900733
Popis: The efficient multifunctionalization by one-pot or cascade catalytic systems has developed as an important research field, but is often challenging due to incompatibilities or cross-reactivities of the catalysts leading to side product formation. Herein we report the stereoselective preparation of cis- and trans-4-aminocyclohexanol from the potentially bio-based precursor 1,4-cyclohexanedione. We identified regio- and stereoselective enzymes catalyzing reduction and transamination of the diketone, which can be performed in a one-pot sequential or cascade mode. For this, we identified regioselective keto reductases for the selective mono reduction of the diketone to give 4-hydroxycyclohexanone. The system is modular and by choosing stereocomplementary amine transaminases, both cis- and trans-4-aminocyclohexanol were synthesized with good to excellent diastereomeric ratios. Furthermore, we identified an amine transaminase that produces cis-1,4-cyclohexanediamine with diastereomeric ratios >98 : 2. These examples highlight that the high selectivity of enzymes enable short and stereoselective cascade multifunctionalizations to generate high-value building blocks from renewable starting materials. Introduction
Databáze: OpenAIRE
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