Related Experiment Video
Updated: Jun 22, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
A synthetic strategy for polyfunctionalized bicyclo[3.3.1]nonanes based on a tandem three-component [3 + 2]
Yu-Long Zhao1, Li Chen, Shao-Chun Yang
1Department of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China. zhaoyl351@nenu.edu.cn
Abstract:
A simple and highly efficient three-component reaction of the readily available alpha-cinnamoyl ketene-S,S-acetals 1 with oxalyl chloride has been developed and the corresponding gamma-alkylidenebutenolides 2 were obtained stereospecifically in excellent yields under very mild conditions. On the basis of this reaction, a series of highly functionalized bicyclo[3.3.1]nonanes 3 were constructed in good to high yields in an atom-economic manner with good diastereoselectivity via a BF3.OEt2-mediated novel tandem double cyclization of gamma-alkylidenebutenolides 2 under very mild conditions.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Related Concept Videos
Cycloaddition Reactions: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: MO Requirements for Thermal Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview