Related Experiment Video
Updated: Sep 29, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Palladium-Catalyzed Enantioselective γ-Arylation of β,γ-Unsaturated Butenolides
Sanliang Li1, Qiaoyu Chen2, Junfeng Yang1
1Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438, China.
Abstract:
γ-Butenolide and γ-butyrolactone scaffolds are two types of important core structures in numerous natural products and bioactive targets. However, methods to construct the chiral quaternary arylated γ-butenolide are rarely explored. We herein report an efficient Pd-catalyzed enantioselective γ-arylation of β,γ-unsaturated butenolides with aryl bromides, which shows high γ-selectivity, good functional group tolerance and excellent enantioselectivity. Notably, this protocol also allows for facile construction of tricyclic tetrahydroindolines and tetrahydroisoquinolinones in one step. DFT calculations are consistent with the experimental results, suggesting that the γ-arylation is favoured over the α-arylation. Finally, this method is applied to the rapid synthesis of natural product (R)-(+)-boivinianin A.
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Hydroboration-Oxidation of Alkenes
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
α-Alkylation of Ketones via Enolate Ions
Radical Anti-Markovnikov Addition to Alkenes: Overview
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

