Structurally divergent dynamic combinatorial chemistry on racemic mixtures.

Nature Communications
Tiberiu-M Gianga, G Dan Pantoș

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.

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Citations

Jun 8, 2021·Chemical Science·Tiberiu-M GiangaG Dan Pantoş
Sep 25, 2021·Journal of the American Chemical Society·Oleg BorodinMax von Delius

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Methods Mentioned

BETA
nuclear magnetic resonance

Software Mentioned

Gabedit
CEM Explorer
Avogadro
COSMO
SDRRM
MOPAC
DCLSim
CEM Discover

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