Chiral self-recognition in a bispericyclic cyclodimerisation reaction of 1-azadienes

Literature Information

Publication Date 2023-10-16
DOI 10.1039/D3QO01562A
Impact Factor 5.281
Authors

Adrián López-Francés, Xabier del Corte, Zuriñe Serna-Burgos, Jesús M. de los Santos, Javier Vicario


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Abstract

Hermaphroditism of molecules: as in nature some species behave as male or female depending on the environment, herein we report a bispericyclic dimerisation of cyclic 1-azadienes where a molecule can behave as either diene or dienophile, depending on its location at the transition state. In a symmetrical reactive complex, here represented by an arbitrary reference system, a molecule that is positioned on top acts as the diene unit, while the dienophile partner is the one situated at the bottom. In addition, a strong chiral self-recognition phenomenon is observed, where each enantiomer within a racemic mixture of chiral 1-azadienes exclusively recognises itself. In order to shed some light into the understanding of the chiral self-recognition effect, an extensive DFT study of the reaction pathway is provided, concluding that a combination of attractive π-stacking forces and repulsive steric interactions is at the origin of the high stereospecificity of the reaction.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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