Related Experiment Video
Updated: Nov 29, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Palladium-Catalyzed Stereoselective Aza-Wacker-Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused
Rong-Shiow Tang1, Li-Yuan Chen1, Chin-Hung Lai2
1School of Pharmacy, China Medical University, Taichung 406040, Taiwan.
Abstract:
Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cis-fused aza-tetracyclic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically, and a probable mechanism was proposed. Strained pentahydrobenzo[f]cyclopenta[hi]indolizin-6-one and racemic γ-lycorane can also be synthesized rapidly using this palladium-catalyzed aza-Wacker-Heck cyclization reaction.
More Related Videos
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

