Double Catalytic Kinetic Resolution (DoCKR) of Acyclic anti -1,3-Diols: The Additive Horeau Amplification - Université de Rennes Accéder directement au contenu
Image (Illustration) Année : 2017

Double Catalytic Kinetic Resolution (DoCKR) of Acyclic anti -1,3-Diols: The Additive Horeau Amplification

Résumé

The concept of a synergistic double catalytic kinetic resolution (DoCKR) as described in this article was successfully applied to racemic acyclic anti-1,3-diols, a common motif in natural products. This process takes advantage of an additive Horeau amplification involving two successive enantioselective organocatalytic acylation reactions, and leads to diesters and recovered diols with high enantiopurities. It was first developed with C2-symmetrical diols and then further extended to non-C2-symmetrical anti diols to prepare useful chiral building blocks. The protocol is highly practical as it only requires 1 mol % of a commercially available organocatalyst and leads to easily separable products. This procedure was applied to the shortest reported total synthesis of (+)-cryptocaryalactone, a natural product with anti-germinative activity.

Dates et versions

medihal-01727652 , version 1 (09-03-2018)

Licence

Domaine public

Identifiants

  • HAL Id : medihal-01727652 , version 1

Citer

Jérémy Mérad, Prashant Borkar, Frédéric Caijo, Jean-Marc Pons, Jean-Luc Parrain, et al.. Double Catalytic Kinetic Resolution (DoCKR) of Acyclic anti -1,3-Diols: The Additive Horeau Amplification. Illustration. France. 2017. ⟨medihal-01727652⟩
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