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 - Aix-Marseille Université Access content directly
Journal Articles Organic Letters Year : 2014

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

Mylène Roudier
  • Function : Author
Thierry Constantieux
  • Function : Author
Adrien Quintard
Jean Rodriguez
  • Function : Author
  • PersonId : 921781

Abstract

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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hal-01066618 , version 1 (22-09-2014)

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Mylène Roudier, Thierry Constantieux, Adrien Quintard, Jean Rodriguez. 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. Organic Letters, 2014, 16, pp.2802. ⟨10.1021/ol500821c⟩. ⟨hal-01066618⟩
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