Enantioselective cascade formal reductive insertion of allylic alcohols into the C(O)Cbond of 1,3-diketones: ready access to synthetically valuable 3-alkylpentanol units

Enantioselective cascade formal reductive insertion of allylic alcohols into the C(O)Cbond of 1,3-diketones: ready access to synthetically valuable 3-alkylpentanol units

An unprecedented cascade reaction combining dual iron−amine-catalyzed enantioselective functionalization of allylic alcohols and chemoselective acyl transfer is presented. It allows, from diketones and allylic alcohols, preparation of efficiently functionalized γ-chiral alcohols in up to 96% yield a...

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Veröffentlicht in:Organic letters 2014-05, Vol.16
Hauptverfasser: Roudier, Mylène, Constantieux, Thierry, Quintard, Adrien, Rodriguez, Jean
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container_title Organic letters
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creator Roudier, Mylène
Constantieux, Thierry
Quintard, Adrien
Rodriguez, Jean
description An unprecedented cascade reaction combining dual iron−amine-catalyzed enantioselective functionalization of allylic alcohols and chemoselective acyl transfer is presented. It allows, from diketones and allylic alcohols, preparation of efficiently functionalized γ-chiral alcohols in up to 96% yield and 96:4 er. The interest of this redox-, atom-, and step-economomical approach was further demonstrated in the short synthesis of several key fragments of biologically active natural products or odorant molecules.
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title Enantioselective cascade formal reductive insertion of allylic alcohols into the C(O)Cbond of 1,3-diketones: ready access to synthetically valuable 3-alkylpentanol units
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