Synthesis of Optically Active syn- and anti-Chlorohydrins through a Bienzymatic Reductive Cascade.
Org Lett
; 24(39): 7082-7087, 2022 Oct 07.
Article
em En
| MEDLINE
| ID: mdl-36154101
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)).
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Base de dados:
MEDLINE
Assunto principal:
Cloridrinas
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article