Chiral Auxiliaries and Chirogenesis

A special issue of Symmetry (ISSN 2073-8994).

Deadline for manuscript submissions: closed (31 December 2017) | Viewed by 47637

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Department of Chemistry and Biotechnology, Tallinn University of Technology, Academia tee 15, 12616 Tallinn, Estonia
Interests: sensors; induced chirality; chirality transfer; supramolecular chirality; chiral chromophores; circular dichroism; chiral materials and surfaces
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Special Issue Information

Dear Colleagues,

Chirality is one of the most fundamental properties of nature and is important in different branches of science, technology, and medicine, relating to the ability of any object to exist as a pair of non-superimposable mirror images or to a unidirectional action (such as motion). The phenomena of chiral auxiliary and chirogenesis are of paramount significance for all aspects of chirality and include asymmetry generation, transfer, amplification, modulation, memorizing, and others. Investigation of these effects is a rapidly growing area of research and directly connects with numerous natural processes, artificial systems, and modern industries. It is widely seen and plays a key role in various biological structures, such as saccharides, proteins, enzymes, membranes, DNA/RNA, etc. In addition, this research field has important practical implications in novel materials, enantioselective catalysis, chiral sensors, optical resolution, asymmetric synthesis, nanotechnology, medicine, pharmacology, biomimetic studies, and others.

The aim of this Special Issue is to highlight and overview all aspects of chiral auxiliary and chirogenesis in different natural/physical sciences and in modern technologies. All types of papers, including comprehensive reviews on general areas, mini reviews on specialized subjects, accounts of own research work, full experimental or theoretical papers, short communications, technical notes, comments, and others are welcome for consideration.

Dr. Victor Borovkov
Guest Editor

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Keywords

  • chirality
  • chirogenesis
  • chiral auxiliary
  • stereochemistry
  • asymmetry
  • optical activity
  • enantiomeric resolution
  • chiroptical spectroscopy
  • chirality devices

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Published Papers (5 papers)

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Research

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17 pages, 8969 KiB  
Article
The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–
by Keiji Hirose, Masaya Ukimi, Shota Ueda, Chie Onoda, Ryohei Kano, Kyosuke Tsuda, Yuko Hinohara and Yoshito Tobe
Symmetry 2018, 10(1), 20; https://doi.org/10.3390/sym10010020 - 9 Jan 2018
Cited by 32 | Viewed by 5587
Abstract
Rotaxanes consisting of achiral axle and achiral ring components can possess supramolecular chirality due to their unique geometrical architectures. To synthesize such chiral rotaxanes, we adapted a prerotaxane method based on aminolysis of a metacyclophane type prerotaxane that had planar chirality, which is [...] Read more.
Rotaxanes consisting of achiral axle and achiral ring components can possess supramolecular chirality due to their unique geometrical architectures. To synthesize such chiral rotaxanes, we adapted a prerotaxane method based on aminolysis of a metacyclophane type prerotaxane that had planar chirality, which is composed of an achiral stopper unit and a crown ether type ring component. The prerotaxanes were well resolved using chiral HPLC into a pair of enantiomerically pure prerotaxanes, which were transferred into corresponding chiral rotaxanes, respectively. Obtained chiral rotaxanes were revealed to have considerable enantioselectivity. Full article
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)
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Review

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26 pages, 80758 KiB  
Review
The Breaking of Symmetry Leads to Chirality in Cucurbituril-Type Hosts
by Riina Aav and Kamini A. Mishra
Symmetry 2018, 10(4), 98; https://doi.org/10.3390/sym10040098 - 5 Apr 2018
Cited by 16 | Viewed by 7986
Abstract
Cucurbituril-type hosts are highly symmetric, but there are means to break their symmetry. This review will present examples from three directions of induction of chirality in or by cucurbituril-type hosts: first, through the incorporation of stereogenic elements into host molecules; second, through complexation [...] Read more.
Cucurbituril-type hosts are highly symmetric, but there are means to break their symmetry. This review will present examples from three directions of induction of chirality in or by cucurbituril-type hosts: first, through the incorporation of stereogenic elements into host molecules; second, through complexation with achiral guests, which leads to axial supramolecular chirality and helical structures; third, through the formation of complexes with chiral guests in multi-molecule complexes and induction of supramolecular chirality. In addition, a list of chiral guests used in binding studies with cucurbiturils is collected. We would envision that encouraged by the outlined examples of outstanding applications of chiral cucurbituril-supramolecular systems, the boundaries of chiral applications of cucurbiturils would be widened. Full article
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)
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75 pages, 44501 KiB  
Review
Chiral Heterocycle-Based Receptors for Enantioselective Recognition
by Vaibhav N. Khose, Marina E. John, Anita D. Pandey, Victor Borovkov and Anil V. Karnik
Symmetry 2018, 10(2), 34; https://doi.org/10.3390/sym10020034 - 24 Jan 2018
Cited by 13 | Viewed by 8441
Abstract
The majority of biomolecules found in living beings are chiral, therefore chiral molecular recognition in living systems is crucial to life. Following Cram’s seminal work on the crown-based chiral recognition, prominent research groups have reported innumerable chiral receptors with distinctly different geometrical features [...] Read more.
The majority of biomolecules found in living beings are chiral, therefore chiral molecular recognition in living systems is crucial to life. Following Cram’s seminal work on the crown-based chiral recognition, prominent research groups have reported innumerable chiral receptors with distinctly different geometrical features and asymmetry elements. Main applications of such chiral receptors are found in chiral chromatography, as for analytical purposes and for bulk separation of racemates.Incorporation of heterocyclic rings in these recognition systems added a new dimension to the existing group of receptors. Heterocycles have additional features such as availability of unshared electron pairs, pronounced conformational features, introduction of hydrogen bonding and presence of permanent dipoles as well as specific spectral properties in certain cases. These features are found to enhance binding properties of the receptors and the selectivity factors between opposite enantiomers, allowing them to be effectively separated. The review presents the synthetic approaches towards these heterocyclic receptors and their distinctly different behavior vis-à-vis carbocyclic receptors. Full article
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)
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13722 KiB  
Review
Helicene-Based Chiral Auxiliaries and Chirogenesis
by Mohammed Hasan and Victor Borovkov
Symmetry 2018, 10(1), 10; https://doi.org/10.3390/sym10010010 - 29 Dec 2017
Cited by 44 | Viewed by 12144
Abstract
Helicenes are unique helical chromophores possessing advanced and well-controlled spectral and chemical properties owing to their diverse functionalization and defined structures. Specific modification of these molecules by introducing aromatic rings of differing nature and different functional groups results in special chiroptical properties, making [...] Read more.
Helicenes are unique helical chromophores possessing advanced and well-controlled spectral and chemical properties owing to their diverse functionalization and defined structures. Specific modification of these molecules by introducing aromatic rings of differing nature and different functional groups results in special chiroptical properties, making them effective chiral auxiliaries and supramolecular chirogenic hosts. This review aims to highlight these distinct structural features of helicenes; the different synthetic and supramolecular approaches responsible for their efficient chirality control; and their employment in the chirogenic systems, which are still not fully explored. It further covers the limitation, scope, and future prospects of helicene chromophores in chiral chemistry. Full article
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)
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6952 KiB  
Review
Chiral Buckybowl Molecules
by Kuppusamy Kanagaraj, Kangjie Lin, Wanhua Wu, Guowei Gao, Zhihui Zhong, Dan Su and Cheng Yang
Symmetry 2017, 9(9), 174; https://doi.org/10.3390/sym9090174 - 30 Aug 2017
Cited by 24 | Viewed by 11855
Abstract
Buckybowls are polynuclear aromatic hydrocarbons that have a curved aromatic surface and are considered fragments of buckminsterfullerenes. The curved aromatic surface led to the loss of planar symmetry of the normal aromatic plane and may cause unique inherent chirality, so-called bowl chirality, which [...] Read more.
Buckybowls are polynuclear aromatic hydrocarbons that have a curved aromatic surface and are considered fragments of buckminsterfullerenes. The curved aromatic surface led to the loss of planar symmetry of the normal aromatic plane and may cause unique inherent chirality, so-called bowl chirality, which it is possible to thermally racemize through a bowl-to-bowl inversion process. In this short review, we summarize the studies concerning the special field of bowl chirality, focusing on recent practical aspects of attaining diastereo/enantioenriched chiral buckybowls through asymmetric synthesis, chiral optical resolution, selective chiral metal complexation, and chiral assembly formation. Full article
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)
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