Asymmetric Reactions

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

Deadline for manuscript submissions: closed (29 September 2020) | Viewed by 2576

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Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, 87030 Arcavacata di Rende (CS), Italy
Interests: the reactivity of organometallic compounds with aromatic systems; the use of dianions derived from enamino carbonyl compounds; the stereoselective reduction of various classes of ketones; the development of new Lewis acid systems; enantioselective organocatalysis
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Special Issue Information

Dear Colleagues,

Asymmetric reactions have assumed growing importance among organic reactions since the beginning of this century. Metal chiral complexes as catalysts, chiral pool, easily available chiral organic products, and chiral organocatalysts have been employed to perform these syntheses.

The widespread dissemination of this topic encouraged me to launch a Special Issue to enrich the knowledge of organic chemists, and, thus, new synthetic methods or reviews collecting data on known reactions are welcome.

This Special Issue will be of interest to organic chemists developing new synthetic methods and others interested in their application to the preparation of chiral organic natural products employable in industry, medicine, and biology.

The audience of potential readers is, therefore, very broad and I hope that many of you contribute your research to this Special Issue.

Prof. Dr. Renato Dalpozzo
Guest Editor

Manuscript Submission Information

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Keywords

  • Asymmetric synthesis
  • Chiral metal catalysis
  • Organocatalysis
  • Chiral pool
  • Heterogeneous catalysis
  • Homogeneous catalysis
  • Asymmetric protecting groups.

Published Papers (1 paper)

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Research

15 pages, 5558 KiB  
Article
Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function
by Abdullah Mohammed Al-Majid, Saied M. Soliman, Matti Haukka, M. Ali, Mohammad Shahidul Islam, Mohammed Rafi Shaik and Assem Barakat
Symmetry 2020, 12(8), 1337; https://doi.org/10.3390/sym12081337 - 10 Aug 2020
Cited by 14 | Viewed by 2279
Abstract
The 1,3-dipolar cycloaddition reaction is one of the most rapid, and efficient protocols to access, and construct highly divergent heterocycle chiral auxiliaries. Free catalyst synthesis of spirooxindole scaffold incorporating sulphone moiety via one pot–three component reaction of 6-chloro-isatin, L-proline, and the phenylvinylsulphone as [...] Read more.
The 1,3-dipolar cycloaddition reaction is one of the most rapid, and efficient protocols to access, and construct highly divergent heterocycle chiral auxiliaries. Free catalyst synthesis of spirooxindole scaffold incorporating sulphone moiety via one pot–three component reaction of 6-chloro-isatin, L-proline, and the phenylvinylsulphone as dienophile is presented. The new regioisomer and diastereomer was isolated by precipitation without the tedious purification step, and then characterized via NMR and single crystal X-ray diffraction analysis. Using Hirshfeld analysis, the analysis of molecular packing was performed. It depended mainly on strong O…H and N…H interactions, and weak H…H, C…H, and Cl…H interactions as well. DFT calculations were used to optimize the experimental X-ray structure, which was found well matched with the calculated one. Reactivity descriptors based on the energies of the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbitals were calculated. Additionally, the donor–acceptor interactions which stabilized the system via σ–σ*, π→π*, n→σ* and n→π* electron delocalization processes were also computed using NBO calculations. The net interaction energies are 49.96, 235.38, 179.66 and 107.06 kJ/mol, respectively. Additionally, the calculated NMR chemical shifts correlated well with the experimental data (R2=0.99). Full article
(This article belongs to the Special Issue Asymmetric Reactions)
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