Related Experiment Video
Updated: May 17, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Benzo-Fused Medium-Sized Heterocycles with a Chiral C-N Axis from Asymmetric Cycloaddition and Skeletal Rearrangement
Luo-Yu Wang1,2, Jiaoting Pan1,2, Mingjin Liu2
1Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, China.
Abstract:
We report an efficient palladium-catalyzed synthesis of diverse enantioenriched benzofused nine- and ten-membered heterocycles featuring a stereogenic carbon as well as an axially chiral N-aryl sulfonamide motif. Such a structural scaffold has shown significant pharmacological potential in related heterocyclic compounds. This method utilizes readily accessible aza-ortho-quinone methide precursors and vinyl carbonates in formal [5 + 4] and [6 + 4] cycloadditions with excellent diastereo- and enantioselectivity. Furthermore, the ten-membered heterocycles can undergo sequential ring-contractive rearrangements, providing systematic access to highly functionalized nine- and eight-membered heterocycles with excellent stereocontrol.
Related Concept Videos
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Prochirality
Stereoisomerism of Cyclic Compounds
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

