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

Abstract : 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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https://hal.archives-ouvertes.fr/hal-03658349
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Submitted on : Tuesday, May 3, 2022 - 6:23:47 PM
Last modification on : Monday, May 16, 2022 - 8:54:40 AM
Long-term archiving on: : Thursday, August 4, 2022 - 6:54:12 PM

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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, Wiley-VCH Verlag, 2022, 2022 (17), pp.e202200031. ⟨10.1002/ejoc.202200031⟩. ⟨hal-03658349⟩

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