Chirality and Symmetry in Stereochemistry

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 January 2022) | Viewed by 3847

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Life Sciences Center, Vilnius University, LT-01513 Vilnius, Lithuania
Interests: chemistry; pharmacology, toxicology and pharmaceutics; biochemistry, genetics and molecular biology; chemical engineering; materials science; physics and astronomy; immunology and microbiology

Special Issue Information

Dear Colleagues,

The different orientations of atoms of molecules in the three-dimensional (3D) orientation in space create plenty of exiting molecular structures and generates the subject of stereochemistry. Stereochemistry spans the entire spectrum of chemistry disciplines, from traditional organic, inorganic, physical chemistry, and biochemistry, to sub-branches, such as supramolecular, organometallic, medicinal, and material chemistry, and also other scientific disciplines.

An extremely important chapter of stereochemistry is chirality. The term chiral is applied to molecules whose asymmetry results in handedness, that is, the existence of a pair of non-superimposable mirror-image shapes as illustrated by the relationship between one's right and left hands. A very important consequence of chirality is that it influences the functional properties of molecules in an enormous way, not only in chemistry and biology, but in mathematics, physics, materials, etc.

The history of chirality began with Louis Pasteur’s discovery of molecular chirality by the separation of chiral crystals of tartaric acid and observing the rotatory effect of enantiomers on a plane of polarised light in 1848. In 2003, the Journal Chemical and Engineering News (2003, 81, 34, 27–30), reported the results of a survey of the journal's readers on ‘‘the most beautiful experiments in the history of chemistry’’. First place was given to Louis Pasteur's manual separation of tartrate enantiomers. William Thompson and Lord Kelvin coined the term "chirality" in 1884.

Recent years have seen an extraordinary development of experimental and theoretical frameworks to study various aspects of chirality. Wide-ranging chiral asymmetry in nature has given rise to a multi-disciplinary interest in chirality.

This Special Issue of Symmetry features articles on chirality in a very extensive stereochemistry field covering both. We are inviting contributions on a broad range of topics across numerous disciplinary boundaries including the following: synthesis and application of chiral molecules and materials; supramolecular chirality; chirality of natural products and in biomolecules for pharmaceutical and agricultural chemistry; development of new and novel applications of known instrumental methods in stereochemistry and chirality, and other comprehensive dimensions in the field without many disciplinary limitations focusing on originality and novelty.

Submit your paper and select the Journal “Symmetry” and the Special Issue “Chirality and Symmetry in Stereochemistry” via: MDPI submission system. Our papers will be published on a rolling basis and we will be pleased to receive your submission once you have finished it.

Prof. Dr. Eugenijus Butkus
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Symmetry is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2400 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Chirality and symmetry
  • Chiral architectures
  • Stereochemistry applications
  • Stereosynthesis
  • Stereochemistry foresight

Published Papers (1 paper)

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Research

17 pages, 2498 KiB  
Article
Highly Diastereoselective Chelation-Controlled 1,3-anti-Allylation of (S)-3-(Methoxymethyl)hexanal Enabled by Hydrate of Scandium Triflate
by Uladzimir S. Masiuk, Iryna V. Mineyeva and Dzmitry G. Kananovich
Symmetry 2021, 13(3), 470; https://0-doi-org.brum.beds.ac.uk/10.3390/sym13030470 - 13 Mar 2021
Cited by 5 | Viewed by 2691
Abstract
En route to the total synthesis of (+)-Neopeltolide, we explored Lewis acid-assisted diastereoselective allylation of MOM-protected 3-hydroxylhexanal with β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane. The hydrated form of scandium triflate was found to be essential for attaining high 1,3-anti-diastereoselectivity (d.r. 94:6), while the use of [...] Read more.
En route to the total synthesis of (+)-Neopeltolide, we explored Lewis acid-assisted diastereoselective allylation of MOM-protected 3-hydroxylhexanal with β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane. The hydrated form of scandium triflate was found to be essential for attaining high 1,3-anti-diastereoselectivity (d.r. 94:6), while the use of anhydrous catalyst resulted in a modest diastereocontrol (d.r. 76:24). The preferred 1,3-anti-selectivity in this transformation can be rationalized in the framework of the Reetz chelate model of asymmetric induction. The 1,3-anti-configuration of the product was confirmed by its conversion into the known C7-C16 building block of (+)-Neopeltolide. We also report an improved protocol for the synthesis of β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane, which can be utilized as a cost-efficient bipolar isoprenoid-type C5-building block in the synthesis of natural compounds. Full article
(This article belongs to the Special Issue Chirality and Symmetry in Stereochemistry)
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