Journal
SYMMETRY-BASEL
Volume 15, Issue 6, Pages -Publisher
MDPI
DOI: 10.3390/sym15061261
Keywords
axial chirality; atropisomer; rotational energy barrier; stereoisomer; amination; C-H activation; annulation; desymmetrization; N-H functionalization
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Atropisomers, which are stereoisomers hindered in their rotation due to steric interactions or electrostatics, exhibit unique characteristics and can be found in various applications. The synthesis of atropisomers containing C-N and N-N axes of chirality has become a hot topic in research, focusing on sustainable synthesis using achiral materials and organocatalysts under mild conditions. This review provides an overview of recent achievements in this field.
Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or by electrostatics, may interact with their surroundings in different ways, and may also exhibit different properties. They may be found as natural products, as pharmaceutical or agricultural active ingredients, as chiral ligands and organocatalysts, and in functional materials. Our ability to synthesize them stereoselectively and in a sustainable way, using achiral materials and simply with the aid of an organocatalyst and mild conditions, has become a hot topic in research. This review provides an overview of recent achievements in the synthesis of atropisomers containing C-N and N-N axes of chirality.
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