Related Experiment Video
Updated: Mar 6, 2026

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
Published on: August 20, 2018
Size- and Shape-Selective Catalytic Dithioacetalization With an Endohedrally Functionalized Self-Assembled Cage
Komal Sharma1, Taehee Kim1, Richard J Hooley1
1Department of Chemistry and the UCR Center for Catalysis, University of California - Riverside, Riverside, California, USA.
None:
An endohedrally functionalized self-assembled Fe4L6 cage complex can catalyze dithioacetal formation from suitably sized and shaped aldehydes and alkanethiols. The cage-catalyzed process is significantly accelerated, compared to small molecule sulfonic acid catalysis, and is selective for dithioacetal formation with fragile allyl-functionalized aldehydes that can otherwise undergo fragmentation and rearrangement. Species with putatively identical reactivity but different shapes show significant differences in conversion: p-anisaldehyde can be easily converted to a range of dithioacetals, but 9-anthraldehyde shows no reactivity. Substantially different reaction rates can be observed for isomeric species as similar as ortho- and para-anisaldehyde. These traits of mechanistic control, size-selectivity, and shape-selectivity are all the hallmarks of enzyme-mimicking catalysis.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

