Catalysis and Synthetic Organic Chemistry

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

Deadline for manuscript submissions: closed (15 December 2021) | Viewed by 2369

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Guest Editor
Studio di Consulenza Scientifica (SCSOP), Via Bornò 5, 23896 Sirtori (LC), Italy
Interests: catalysis; green chemistry; organic chemistry; asymmetric synthesis; industrial applications

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Guest Editor
Dipartimento di Scienza e Alta Tecnologia, Università degli studi dell'Insubria, Via Valleggio 11, 22100 Como, Italy
Interests: stereoselective catalysis; chirality; organic chemistry; organic semiconductors
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Special Issue Information

Dear Colleagues,

An unsymmetrical arrangement of atoms in a molecule determines a discriminatory interaction with molecules with the same property and generates positive, negative or sometimes neutral effects. As a result, many biological events are greatly influenced by the chirality of molecules. Many drugs, phytodrugs, nutraceuticals, aromas, and fragrances have this characteristic, and cells of living organisms can sense this “surface chirality” and exhibit much different adhesion and activation behaviors on enantiomorphic surfaces. For a synthetic organic chemist, the preparation of these enantioenriched molecules may be a challenge, and chemo- and/or bio-catalysis is a useful tool in their hands. For a more sustainable production of these targets with fewer waste by-products, catalyzed enantio- or diastereoselective synthesis, as well as catalyzed racemization of unwanted stereoisomers, are required, but without neglecting an economic assessment.

Papers and reviews on efficient catalyzed methodologies as well as contributions for identifying cost and technical bottlenecks in catalyzed processes are welcome.

Dr. Oreste Piccolo
Prof. Dr. Tiziana Benincori
Guest Editors

Manuscript Submission Information

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Keywords

  • enantioselective catalysis
  • chemocatalysis
  • biocatalysis
  • asymmetric synthesis
  • enantioselective desymmetrization
  • catalyzed kinetic resolution
  • catalyzed racemization
  • chirality amplification
  • green and sustainable chemistry
  • industrial applications

Published Papers (1 paper)

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Research

16 pages, 5308 KiB  
Article
Stereoselective Synthesis of Chiral α-SCF3-β-Ketoesters Featuring a Quaternary Stereocenter
by Monica Fiorenza Boselli, Chiara Faverio, Elisabetta Massolo, Laura Raimondi, Alessandra Puglisi and Maurizio Benaglia
Symmetry 2021, 13(1), 92; https://doi.org/10.3390/sym13010092 - 07 Jan 2021
Cited by 1 | Viewed by 1879
Abstract
The development of new and efficient methods, reagents, and catalysts for the introduction of fluorine atoms or fluorinated moieties in molecular scaffolds has become a topic of paramount importance in organic synthesis. In this framework, the incorporation of the SCF3 group into [...] Read more.
The development of new and efficient methods, reagents, and catalysts for the introduction of fluorine atoms or fluorinated moieties in molecular scaffolds has become a topic of paramount importance in organic synthesis. In this framework, the incorporation of the SCF3 group into organic molecule has often led to beneficial effects on the drug’s metabolic stability and bioavailability. Here we report our studies aimed to the stereoselective synthesis of chiral α-SCF3-β−ketoesters featuring a tetrasubstituted stereocenter. The use of a chiral auxiliary was crucial to synthesize enantiopure enamines that were reacted with N-trifluoromethylthio saccharin or phthalimide, to afford enantioenriched α-SCF3-tetrasubstitued β-keto esters. By using a readily available, inexpensive chiral diamine, such as trans-1,2-diaminocyclohexane, the fluorinated products could be obtained in modest to good yields, and, after the removal of the chiral auxiliary, α-substituted- α trifluoromethylthio-β−ketoesters were isolated with high enantioselectivity (up to 91% ee). Full article
(This article belongs to the Special Issue Catalysis and Synthetic Organic Chemistry)
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