Multi-catalytic Enantioselective Synthesis of 1,3-Diols Containing a Tetrasubstituted Fluorinated Stereocenter
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 organocatalyzed fluorination of alpha-disubstituted aldehydes followed by a diastereoselective copper-catalyzed decarboxylative aldol reaction. Reduction of the generated beta-hydroxy ketone followed by a Lewis base-catalyzed kinetic resolution enables the isolation of original fluorinated 1,3-diols with perfect diastereo- and enantio-control.
Références
- Titre
- Multi-catalytic Enantioselective Synthesis of 1,3-Diols Containing a Tetrasubstituted Fluorinated Stereocenter
- Type de publication
- Article de revue
- Année de publication
- 2022
- Auteurs
- Shao, Na, Monnier Valérie, Charles Laurence, Rodriguez Jean, Bressy Cyril, and Quintard Adrien
- Revue
- European Journal of Organic Chemistry
- Volume
- 2022
- Ticket
- 17
- Pagination
- e202200031
Soumis le 7 septembre 2022