Journal
ACS CATALYSIS
Volume 8, Issue 3, Pages 2413-2419Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03293
Keywords
laccases; ene-reductases; oxidation; allylic alcohols; redox isomerization
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Funding
- MICINN [CTQ2013-44153-P, CTQ2016-75752-R]
- Regional Government from the Principado de Asturias [FC-15-GRUPIN14-002]
- Regional Government from the Principado de Asturias
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The design of catalytic oxidative methodologies in aqueous medium under mild reaction conditions and using molecular oxygen as final electron acceptor represents a suitable alternative to the traditional oxidative transformations. These methods are especially relevant if other functionalities that can be oxidized are present within the same molecule, as in the case of allylic alcohols. Herein we apply a simple chemoenzymatic system composed of the laccase from Trametes versicolor and 2,2,6,6-tetramethylpiperidinyloxy radical (TEMPO) to oxidize a series of racemic allylic sec-alcohols into the corresponding alpha,beta-unsaturated ketones. Afterward, these compounds react with different commercially available ene-reductases to afford the corresponding saturated ketones. Remarkably, in the case of trisubstituted alkenes, the bioreduction reaction occurred with high stereoselectivity. Overall, a bienzymatic one-pot two-step sequential strategy has been described with respect to the synthesis of saturated ketones starting from racemic allylic alcohols, thus resembling the metal-catalyzed redox isomerizations of these derivatives that have been previously reported in the literature.
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