Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
نویسندگان
چکیده
Due to their well-defined three-dimensional geometry, spiro compounds are widely utilized in drug research. From the central tetrahedral carbon atom, besides the regular structure, an inverted spiro connectivity may be envisioned. Here we disclose the synthesis of this molecule class that we have coined quasi[1]catenanes. Next to their fascinating and aesthetic shape, the higher compactness as compared to regular spiro bicycles is noteworthy. To enable synthetic access to compact entangled multimacrocyclic molecules, we have developed a new strategy. The key element is a template, which is covalently connected to the linear precursors, and spatially directs the sterically congested backfolding macrocyclizations that are required to give quasi[1]catenanes. Similarly, quasi[1]rotaxanes are made.
منابع مشابه
Anion templated assembly of mechanically interlocked structures.
This tutorial review describes the evolution of the field of chemical templation, in particular, emphasising the impact its application has made to the synthesis of mechanically interlocked structures. Recent advances in the use of negatively charged template species for the synthesis of interlocked structures are detailed, with the main focus of this review describing the development of a gene...
متن کاملMetal-organic frameworks incorporating copper-complexed rotaxanes.
The incorporation of mechanically interlocked molecules (MIMs), such as rotaxanes and catenanes, into porous metal– organic frameworks (MOFs) has recently been recognized as a strategy for introducing dynamics into otherwise rigid, robust frameworks. In this manner, the interlocked nature of these switchable components allows dynamics to be expressed independently of the MOF backbone and, there...
متن کاملRotaxanes and catenanes as prototypes of molecular machines and motors*
In the course of the last 20 years, our view on rotaxanes and catenanes has completely changed. Copper(I)-templated strategies, in particular, have allowed us to prepare catenanes on a real preparative scale, in a few chemical steps from commercially available compounds. A particularly significant improvement was the introduction of the recently developed ring-closing metathesis reaction, using...
متن کاملChemical consequences of mechanical bonding in catenanes and rotaxanes: isomerism, modification, catalysis and molecular machines for synthesis.
Research on mechanically interlocked molecules has advanced substantially over the last five decades. A large proportion of the published work focusses on the synthesis of these challenging targets, and the subsequent control of the relative position of the covalent sub-components, to generate novel molecular devices and machines. In this Feature Article we instead review some of the less discu...
متن کاملTheoretical Study Of A Switchable [2]-Rotaxane
In recent years, pioneering work carried out by Sauvage, Stoddart and co-workers [1], , has focused on the development of synthetic methodologies and the characterization of catenanes and rotaxanes. Catenanes and rotaxanes are examples of interlocked molecule. Unlike classical molecular structures, they consist of two or more separate components which are mechanically connected. Catenanes consi...
متن کامل