From oximes to tertiary alcohols in water, at room temperature and under air: a hybrid one-pot tandem assembly of enzymatic deoximation and RLi/RMgX reagents.

Org Biomol Chem

Laboratorio de Química Sintética Sostenible (QuimSinSos), Departamento de Química Orgánica e Inorgánica, (IUQOEM), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Química, Universidad de Oviedo, E33071 Oviedo, Spain.

Published: May 2023

AI Article Synopsis

  • A new efficient method has been developed for synthesizing tertiary alcohols using a combination of an enzyme system (laccase/TEMPO/O) and polar organometallic reagents (RLi/RMgX).
  • This hybrid one-pot tandem approach allows for fast and selective reactions under mild, non-traditional conditions, such as room temperature and without a protective atmosphere.
  • The process eliminates the need for complex intermediate purification steps, making it a more streamlined and convenient alternative in organic synthesis.

Article Abstract

The highly efficient biodeoximation of aromatic ketoximes, promoted by the enzymatic oxidative system laccase/TEMPO/O, has been successfully assembled with the fast and chemoselective addition of highly-polar s-block organometallic reagents (RLi/RMgX) to highly-substituted tertiary alcohols. By using this hybrid one-pot tandem protocol, tertiary alcohols have been selectively synthesized in good yields and under mild and bench-type reaction conditions (room temperature, the absence of a protecting atmosphere and aqueous media, which are non-typical conditions for polar organometallic reagents). The overall hybrid one-pot tandem transformation amalgamates two distant organic synthetic tools (RLi/RMgX reagents and enzymes) without the need for any tedious and energy/time-consuming intermediate isolation/purification steps.

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Source
http://dx.doi.org/10.1039/d3ob00285cDOI Listing

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