Spontaneous macrocyclization through multiple dynamic cyclic aminal formation

The use of aminals in dynamic covalent chemistry is slightly underexplored, probably due to their inherent instability. Here we report the spontaneous [2+2] macrocyclization of tetrakis(aminals). Their unexpected stability and structural modularity, the dynamic nature of the connections and their wa...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-02, Vol.57 (1), p.119-1193
Main Authors: Carbajo, Daniel, Ruiz-Sánchez, Antonio Jesús, Nájera, Francisco, Pérez-Inestrosa, Ezequiel, Alfonso, Ignacio
Format: Article
Language:English
Subjects:
Dynamic stability
Modularity
Structural stability
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The use of aminals in dynamic covalent chemistry is slightly underexplored, probably due to their inherent instability. Here we report the spontaneous [2+2] macrocyclization of tetrakis(aminals). Their unexpected stability and structural modularity, the dynamic nature of the connections and their water tolerance make them appealing systems for future applications as stimulus-responsive materials. The efficient cyclic aminal formation leads to the stereoselective synthesis of the corresponding [2+2] macrocycles, for which the dynamic covalent nature of the aminal bond can be controlled under specific conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07184f