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Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones

Research output: Contribution to Journal/MagazineJournal articlepeer-review

<mark>Journal publication date</mark>5/08/2022
<mark>Journal</mark>The Journal of Organic Chemistry
Number of pages21
Pages (from-to)10256–10276
Publication StatusPublished
Early online date8/07/22
<mark>Original language</mark>English


As saturated heterocyclic building blocks become increasingly popular in medicinal chemistry and drug discovery programs, expansion of the synthetic toolkit to novel stereofunctionalized heterocycles is a priority. Herein, we report the development of a palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction to access a broad range of enantioenriched α-difunctionalized 5- and 6-membered sulfones from easily accessible racemic starting materials. The allylic alkylation step was found to occur with high levels of enantioselectivity as a result of a palladium-mediated dynamic kinetic resolution of E/Z enolate intermediates. This methodology paves the way to hitherto unexplored stereodefined cyclic sulfones for medicinal chemistry applications.