Related Experiment Video
Updated: Sep 18, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Synthesis and Characterization of Atropdiastereomeric Macrocyclic Metacyclophanes
Shengkai Wei1, Liang-Yu Chen1, Junqi Li1
1Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.
None:
We report the design, synthesis, and characterization of achiral macrocyclic metacyclophanes exhibiting atropdiasteromerism. These macrocycles contain a 1,2,6-trisubstituted benzene in which the 1 position bears an amide group and the 2 and 6 positions are connected by a bridging chain. Because of the hindered rotation about the C(aryl)-C(acyl) bond and C(sp2)-C(sp3) bonds, the C═O bond of the amide group may be oriented toward or away from the interior of the macrocycle, resulting in observable and separable stereoisomers.
Related Concept Videos
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Stereoisomerism of Cyclic Compounds
Cycloaddition Reactions: Overview
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)