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Symmetry
Special Issues
Asymmetric Centers in Optically Active Molecules Containing a Heteroatom
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Asymmetric Centers in Optically Active Molecules Containing a Heteroatom

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

Deadline for manuscript submissions: 20 December 2024 | Viewed by 6306

Special Issue Editors

Prof. Dr. György Keglevich

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Guest Editor
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary
Interests: organophosphorus chemistry; P-heterocycles; phosphonic and phosphinic derivatives; bisphosphonates; green chemistry; microwave assistance; ionic liquids; catalysts; solvent-free reactions; P-C couplings; flow chemistry; pharmaceutical developments
Special Issues, Collections and Topics in MDPI journals
Dr. Péter Bagi

E-Mail Website
Guest Editor
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary
Interests: P-stereogenic compounds; organophosphorus chemistry; optically active compounds; catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is devoted advances in the chemistry of optically active compounds containing non-common heteroatoms, like S, P, Si, and B. The asymmetric center(s) may be in the heteroatom itself or in other parts of the molecular structure. The Special Issue welcomes regular research papers, reviews, and short communications in this field. Relevant topics include asymmetric hetereoatom-contacting organic and organometallic syntheses, and optical resolutions. Synthetic strategies and methodologies, applications of chiral auxiliaries or catalysts, transition metal complexes of P-ligands, the application of homogeneous catalysis, methods for the separation of enantiomers, theoretical or spectroscopic aspects, as well as physicochemical or biological activities of stereoisomers may be discussed in this scientific paper.

Prof. Dr. György Keglevich
Dr. Péter Bagi
Guest Editors

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

  • organometallic syntheses
  • heteroatomic asymmetry center
  • P-stereogenic center
  • asymmetric syntheses
  • enantioselective syntheses
  • resolution of racemates
  • optically active ligands
  • chiral P-ligands
  • homogeneous catalysis
  • transition metal complexes
  • chiral auxiliaries
  • chiral catalysts

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Published Papers (3 papers)

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Research

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15 pages, 2061 KiB  
Article
Synthesis of α-Hydroxyethylphosphonates and α-Hydroxyethylphosphine Oxides: Role of Solvents During Optical Resolution
by Zsuzsanna Szalai, Anna Sára Kis, József Schindler, Konstantin Karaghiosoff and György Keglevich
Symmetry 2024, 16(11), 1557; https://doi.org/10.3390/sym16111557 - 20 Nov 2024
Viewed by 377
Abstract
Five chiral, racemic dialkyl α-hydroxyethylphosphonates and α-hydroxyethyl-diarylphosphine oxides were prepared in a scalable manner. Possibilities for the optical resolution of the racemic hydroxyphosphine oxides were explored via diastereomeric complex-forming experiments. The acidic calcium salt of O,O′-dibenzoyl-(2R,3R)-tartaric [...] Read more.
Five chiral, racemic dialkyl α-hydroxyethylphosphonates and α-hydroxyethyl-diarylphosphine oxides were prepared in a scalable manner. Possibilities for the optical resolution of the racemic hydroxyphosphine oxides were explored via diastereomeric complex-forming experiments. The acidic calcium salt of O,O′-dibenzoyl-(2R,3R)-tartaric acid and O,O′-di-p-tolyl-(2R,3R)-tartaric acid were chosen as the resolving agents. The role of the solvent in the enantiomeric discrimination was investigated. The diastereomeric complex could be obtained in a crystalline form for α-hydroxyethyl-diphenylphosphine oxide and α-hydroxyethyl-bis(4-methylphenyl)phosphine oxide. However, in the third case, for α-hydroxyethyl-bis(3,5-dimethylphenyl)phosphine oxide, there was no chiral discrimination. Decomposition of the recrystallized diastereomeric complex followed by decomposition of the complex yielded the target compounds in 77/90% enantiomeric excess. The absolute configuration of the hydroxyethyl-diphenylphosphine oxide was determined by single-crystal X-ray diffraction measurements. The interactions stabilizing the supramolecular associate were evaluated. Full article
(This article belongs to the Special Issue Asymmetric Centers in Optically Active Molecules Containing a Heteroatom)
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19 pages, 7215 KiB  
Article
Myrtenal and Myrtanal as Auxiliaries in the Synthesis of Some C,P-Stereogenic Hydroxyphosphine Oxides and Hydroxyphosphine-Boranes Possessing up to Four Contiguous Centers of Chirality
by K. Michał Pietrusiewicz, Anna E. Kozioł, Hanna Małuszyńska and Sylwia Sowa
Symmetry 2023, 15(6), 1172; https://doi.org/10.3390/sym15061172 - 30 May 2023
Cited by 1 | Viewed by 1690
Abstract
1,4- and 1,2-additons of secondary phosphine oxides to (1R)-myrtenal and (1S)-myrtanal were evaluated as potential routes to P,C-stereogenic phosphine oxides bearing additional hydroxyl or aldehyde functions. 1,4-Additions of racemic secondary phosphine oxides to (1R)-myrtenal were found to [...] Read more.
1,4- and 1,2-additons of secondary phosphine oxides to (1R)-myrtenal and (1S)-myrtanal were evaluated as potential routes to P,C-stereogenic phosphine oxides bearing additional hydroxyl or aldehyde functions. 1,4-Additions of racemic secondary phosphine oxides to (1R)-myrtenal were found to offer moderate to good stereoselectivity which shows some promise for utility in kinetic resolution processes, especially at lower conversions. In case of 1,2-additions making the process doubly asymmetric by using an enantiomerically pure secondary phosphine oxide as substrate turned out to be practical. The stereochemical course of the addition reactions under study is presented. The P-resolved 1,2-addition products were demonstrated to undergo facile reduction by BH3 at room temperature leading to the formation of the corresponding α-hydroxyphosphine-boranes with clean inversion of configuration at the P-centre. All P,C-stereogenic phosphine oxides and boranes that were isolated in the form of a single diastereoisomer were assigned their absolute configurations by means of X-ray crystallography and/or 2D NMR spectral techniques. Full article
(This article belongs to the Special Issue Asymmetric Centers in Optically Active Molecules Containing a Heteroatom)
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Review

Jump to: Research

56 pages, 57303 KiB  
Review
Catalytic Asymmetric Synthesis of C-Chiral Phosphonates
by Anastasy O. Kolodiazhna and Oleg I. Kolodiazhnyi
Symmetry 2022, 14(9), 1758; https://doi.org/10.3390/sym14091758 - 23 Aug 2022
Cited by 10 | Viewed by 2850
Abstract
The current review is devoted to the achievements in the development of methods for the catalytic asymmetric synthesis of phosphonates containing a chiral center in the side chain. C-chiral phosphonates are widely represented among natural compounds with various biological activities as insecticides, herbicides, [...] Read more.
The current review is devoted to the achievements in the development of methods for the catalytic asymmetric synthesis of phosphonates containing a chiral center in the side chain. C-chiral phosphonates are widely represented among natural compounds with various biological activities as insecticides, herbicides, antibiotics, and bioregulators. Synthetic representatives of this class have found practical application as biologically active compounds. The review summarizes methods of asymmetric metal complex catalysis and organocatalysis as applied to such reactions as phospha-aldol reaction, two-component and three-component phospha-Mannich reaction, phospha-Michael reaction, as well as hydrogenation of unsaturated phosphonates and phosphine oxides, ketophosphonates, and iminophosphonates. Methods for the asymmetric hydride reduction of C=X phosphonates (X=O, S, NR) are also discussed in detail. The review presents updated literature reports, as well as original research by the author. Full article
(This article belongs to the Special Issue Asymmetric Centers in Optically Active Molecules Containing a Heteroatom)
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