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

Organic Letters, ISSN: 1523-7052, Vol: 16, Issue: 11, Page: 2802-2805
2014
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Article 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. © 2014 American Chemical Society.

Bibliographic Details

Roudier, Mylène; Constantieux, Thierry; Quintard, Adrien; Rodriguez, Jean

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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