Abstract
Structurally Divergent Reactions on Racemic Mixtures are atypical processes in Nature. The few examples reported in the literature take place in organic solvents and are driven by the reagents’ interaction with bulky chiral catalysts. Herein, we describe a dynamic combinatorial approach to generate structural divergence from racemic building blocks. The divergence is due to a stereospecific electron-donor – electron-acceptor interaction of diastereomeric macrocycles, leading to structurally distinct pseudorotaxanes. The equilibrated dynamic combinatorial library contains, amongst various macrocycles, two different types of [2]catenanes that are non-isomeric. The formation of these [2]catenanes is due to a spontaneous stereo and structurally divergent assembly of the building blocks.
Highlights
Divergent Reactions on Racemic Mixtures are atypical processes in Nature
While the synthesis of [2]catenanes is in and of itself exciting, this work is set apart by the discovery of a different type of SDRRM driven by supramolecular interactions
This can open the door for the development of other divergent reactions on racemic mixtures based on aqueous, metal-free chemistry
Summary
Divergent Reactions on Racemic Mixtures are atypical processes in Nature. The reactions take place under the conditions of disulphide exchange in aqueous dynamic combinatorial libraries (DCL) and the resulting products are in stark contrast to our previous work, where enantiomers lead to the formation of diastereomers when reacted with a chiral building block[9,10]. In this dynamic combinatorial chemistry (DCC) system, the divergence is due to a combination of the assembly of diastereomeric macrocycles and a stereospecific electron-donor (D) – electron-acceptor (A) interaction, leading to structurally distinct pseudorotaxanes. This work enhances our understanding of SDRRMs and raises the possibility of supramolecular interactions in aqueous media, playing a crucial role in biological homochirality[11,12,13]
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