From a Sequential to a Concurrent Reaction in Aqueous Medium: Ruthenium-Catalyzed Allylic Alcohol Isomerization and Asymmetric Bioreduction.
The ruthenium-catalyzed redox isomerization of allylic alcohols was successfully coupled with the enantioselective enzymatic ketone reduction (mediated by KREDs) in a concurrent process in aqueous medium. The overall transformation, formally the asymmetric reduction of allylic alcohols, took place with excellent conversions and enantioselectivities, under mild reaction conditions, employing commercially and readily available catalytic systems, and without external coenzymes or cofactors. Optimization resulted in a multistep approach and a genuine cascade reaction where the metal catalyst and biocatalyst coexist from the beginning.
EntreChem SL, Edificio Científico Tecnológico, Campus El Cristo, 33006, Oviedo, Spain.
Nicolás
N
Ríos-Lombardía
Laboratorio de Compuestos OrganometálicosyCatálisis (Unidad Asociada al CSIC), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071, Oviedo, Spain.
Cristian
C
Vidal
EntreChem SL, Edificio Científico Tecnológico, Campus El Cristo, 33006, Oviedo, Spain.
Elisa
E
Liardo
EntreChem SL, Edificio Científico Tecnológico, Campus El Cristo, 33006, Oviedo, Spain.
Francisco
F
Morís
Laboratorio de Compuestos OrganometálicosyCatálisis (Unidad Asociada al CSIC), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071, Oviedo, Spain. garciajoaquin@uniovi.es.
Joaquín
J
García-Álvarez
EntreChem SL, Edificio Científico Tecnológico, Campus El Cristo, 33006, Oviedo, Spain. jgsabin@entrechem.com.
Javier
0000-0003-3764-4750
J
González-Sabín
alcohols; chirality; enzyme catalysis; isomerization; transition metals