Multi‐catalytic Enantioselective Synthesis of 1,3‐Diols Containing a Tetrasubstituted Fluorinated Stereocenter - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

Multi‐catalytic Enantioselective Synthesis of 1,3‐Diols Containing a Tetrasubstituted Fluorinated Stereocenter

Résumé

The enantioselective construction of fluorohydrins featuring a tetrasubstituted stereocenter embedded in complex frameworks represents an important challenge. Herein, we report a multicatalytic strategy enabling the stereoselective preparation of a new type of scaffold containing such a challenging fluorohydrin motif. The sequence is based on an organo-catalyzed fluorination of α-disubstituted aldehydes followed by a diastereoselective copper-catalyzed decarboxylative aldol reaction. Reduction of the generated β-hydroxy ketone followed by a Lewis base-catalyzed kinetic resolution enables the isolation of original fluorinated 1,3-diols with perfect diastereoand enantio-control.
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Dates et versions

hal-03658349 , version 1 (03-05-2022)

Identifiants

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Na Shao, Valérie Monnier, Laurence Charles, Jean Rodriguez, Cyril Bressy, et al.. Multi‐catalytic Enantioselective Synthesis of 1,3‐Diols Containing a Tetrasubstituted Fluorinated Stereocenter. European Journal of Organic Chemistry, 2022, 2022 (17), pp.e202200031. ⟨10.1002/ejoc.202200031⟩. ⟨hal-03658349⟩

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