Related Experiment Video
Updated: Jul 30, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Towards the Total Synthesis of Saponaceolides: Synthesis of cis-2,4-Disubstituted 3,3-Dimethylmethylenecyclohexanes
1Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA).
Abstract:
Controlling diastereoselectivity by metal coordination: In the case of 3,3-dimethylmethylenecyclohexanes 2-a structural unit present in many interesting natural products-the thermodynamically less stable cis-2,4-disubstituted compounds become available through a cyclization event wherein the configuration is determined by a carbopalladation step. Both the cycloisomerization of 1,7-enynes 1 and the intramolecular Heck-type reaction of compounds of type 3 provide the cis product as the major product.
Related Concept Videos
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stereoisomerism of Cyclic Compounds
Preparation and Reactions of Sulfides
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
