Synthesis of Optically Active syn - and anti -Chlorohydrins through a Bienzymatic Reductive Cascade.

Autor:	González-Rodríguez J; Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería s/n, 33006 Oviedo, Spain., Albarrán-Velo J; Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería s/n, 33006 Oviedo, Spain., Soengas RG; Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería s/n, 33006 Oviedo, Spain., Lavandera I; Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería s/n, 33006 Oviedo, Spain., Gotor-Fernández V; Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería s/n, 33006 Oviedo, Spain., Rodríguez-Solla H; Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería s/n, 33006 Oviedo, Spain.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2022 Oct 07; Vol. 24 (39), pp. 7082-7087. Date of Electronic Publication: 2022 Sep 26.
DOI:	10.1021/acs.orglett.2c02592
Abstrakt:	A bienzymatic cascade has been designed and optimized to obtain enantiopure chlorohydrins starting from the corresponding 1-aryl-2-chlorobut-2-en-1-ones. For the synthesis of these α-chloroenones, a two-step sequence was developed consisting of the allylation of the corresponding aldehyde with 3-dichloroprop-1-ene, followed by oxidation and further isomerization. The selective cooperative catalytic system involving ene-reductases (EREDs) and alcohol dehydrogenases (ADHs) afforded the desired optically active chlorohydrins under mild reaction conditions in excellent conversions (up to >99%) and selectivities (up to >99:1 diastereomeric ratio (dr), >99% enantiomeric excess ( ee )).
Databáze:	MEDLINE
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