Síntesis de Sin- y anti -clorhidrinas ópticamente activas a través de una cascada bienzimática reductiva

  1. Jorge González Rodríguez 1
  2. Jesús Albarrán Velo 1
  3. Raquel G Soengas 1
  4. Vicente Gotor Fernández 1
  5. Humberto Rodríguez Solla 1
  1. 1 Universidad de Oviedo
    info
    Universidad de Oviedo

    Oviedo, España

    ROR https://ror.org/006gksa02

    Geographic location of the organization Universidad de Oviedo
Journal:
Boletín de Ciencias y Tecnología

ISSN: 2695-2815

Year of publication: 2023

Issue: 57

Pages: 343-353

Type: Article

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Abstract

A bienzymatic cascade has been designed and optimized to obtain enantiopure chlorohydrins starting from the correspondint 1-+aryl-2 chlorobut-2-en-1-ones. For the preparation of these initial α-chloroenone, a synthetic sequience was developed consisting of the allylation of the corresponding aldehyde with 3-dichloroprop-1-ene, followed by alcohol oxidation and further isomerization of the intermediate ketone. Next, the selective cooperative catalytic action of an ene-reductase and an alcohol dehydrogenase, afforded the desired optically active clorohydrins under mild reaction conditions in excellent conversions (up to >99%) and selectivities (up to 99:1 diastereomeric ratio, >99% enantiomeric excess)

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