Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones

Bowen, Eleanor and Laidlaw, Gillian and Atkinson, Bethany and McArdle-Ismaguilov, Timur and Franckevicius, Vilius (2022) Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones. The Journal of Organic Chemistry. 10256–10276.

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Abstract

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.

Item Type:
Journal Article
Journal or Publication Title:
The Journal of Organic Chemistry
ID Code:
173819
Deposited By:
Deposited On:
29 Jul 2022 14:25
Refereed?:
Yes
Published?:
Published
Last Modified:
15 Aug 2022 11:50