Related Experiment Video
Updated: Sep 29, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium/Chiral-Diene-Catalyzed Switchable Asymmetric Divergent Arylation of Enone-Diones
Junbao Li1, Jinghui Sun1, Wenzhu Ren1
1College of Materials, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China.
Abstract:
A rhodium/chiral diene catalytic system is reported for the reaction of enone-diones and arylboronic acids that allows the switchable synthesis of chiral bicyclic products and acyclic products in a controlled manner. The production of bicyclic products containing four contiguous stereocenters is assumed to proceed through the enantioselective arylrhodation of enone-diones with Cs2CO3, forming a rhodium-enolate intermediate, followed by desymmetrization of the diastereotopic diones via aldol cyclization with quantitative diastereoselection and excellent enantiomeric excess. The production of acyclic products is assumed to proceed through the enantioselective hydroarylation of enone-diones with excellent enantiomeric excess in which the aldol cyclization is significantly inhibited by the choice of Et3N as a base. The selectivity for bicyclic products (via tandem arylation-aldol cyclization) and acyclic products (via hydroarylation) is rationalized by the proposed model.
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...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Stereochemical Effects of Enolization

