Recent Advances in the Field of Non-common Heteroatom-Containing, Optically Active Molecules

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

Deadline for manuscript submissions: closed (30 June 2021) | Viewed by 13050

Special Issue Editors

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
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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. György Keglevich
Dr. Péter Bagi
Guest Editors

Manuscript Submission Information

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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.

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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

Published Papers (3 papers)

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Research

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27 pages, 5532 KiB  
Article
Efficient Oxidative Resolution of 1-Phenylphosphol-2-Ene and Diels–Alder Synthesis of Enantiopure Bicyclic and Tricyclic P-Stereogenic C-P Heterocycles
by K. Michał Pietrusiewicz, Marek Koprowski, Zbigniew Drzazga, Renata Parcheta, Elżbieta Łastawiecka, Oleg M. Demchuk and Iwona Justyniak
Symmetry 2020, 12(3), 346; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12030346 - 01 Mar 2020
Cited by 6 | Viewed by 2587
Abstract
1-Phenylphosphol-2-ene 1-oxide is effectively resolved by L-menthyl bromoacetate to afford both SP and RP enantiomers of 1-phenylphosphol-2-ene 1-oxide on a multigram scale. The resolved 1-phenylphosphol-2-ene oxide has been found to undergo face-selective and endo-selective cycloadditions with a series of acyclic and [...] Read more.
1-Phenylphosphol-2-ene 1-oxide is effectively resolved by L-menthyl bromoacetate to afford both SP and RP enantiomers of 1-phenylphosphol-2-ene 1-oxide on a multigram scale. The resolved 1-phenylphosphol-2-ene oxide has been found to undergo face-selective and endo-selective cycloadditions with a series of acyclic and cyclic dienes to produce enantiopure P-stereogenic C-P heterocycles of hexahydrophosphindole and hexahydrobenzophosphindole as well as phospha[5.2.1.02,6]decene and phospha[5.2.2.02,6]undecene structures. Conversions of these cycloadducts to the fully saturated heterocyclic systems as well as to their P (III), P = S, P = Se and P-BH3 derivatives have been demonstrated to occur with retention of configuration and preservation of configurational homogeneity at P. A perplexing case of stereomutation at P during reduction of a tricyclic β-hydroxy phosphine oxide by PhSiH3 at 80 °C has been recorded. Full article
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Review

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24 pages, 14097 KiB  
Review
Optically Active Selenoxides: Structural and Synthetic Aspects
by Dorota Krasowska, Luca Sancineto, Małgorzata Deska and Józef Drabowicz
Symmetry 2020, 12(3), 349; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12030349 - 01 Mar 2020
Cited by 4 | Viewed by 2903
Abstract
Synthetic approaches to the preparation of non-racemic selenoxides and the problem of their optical stability are discussed in this mini review. Full article
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52 pages, 51178 KiB  
Review
Asymmetric Electrophilic Reactions in Phosphorus Chemistry
by Anastasy O. Kolodiazhna and Oleg I. Kolodiazhnyi
Symmetry 2020, 12(1), 108; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12010108 - 06 Jan 2020
Cited by 12 | Viewed by 6824
Abstract
This review is devoted to the theoretic and synthetic aspects of asymmetric electrophilic substitution reactions at the stereogenic phosphorus center. The stereochemistry and mechanisms of electrophilic reactions are discussed—the substitution, addition and addition-elimination of many important reactions. The reactions of bimolecular electrophilic substitution [...] Read more.
This review is devoted to the theoretic and synthetic aspects of asymmetric electrophilic substitution reactions at the stereogenic phosphorus center. The stereochemistry and mechanisms of electrophilic reactions are discussed—the substitution, addition and addition-elimination of many important reactions. The reactions of bimolecular electrophilic substitution SE2(P) proceed stereospecifically with the retention of absolute configuration at the phosphorus center, in contrast to the reactions of bimolecular nucleophilic substitution SN2(P), proceeding with inversion of absolute configuration. This conclusion was made based on stereochemical analysis of a wide range of trivalent phosphorus reactions with typical electrophiles and investigation of examples of a sizeable number of diverse compounds. The combination of stereospecific electrophilic reactions and stereoselective nucleophilic reactions is useful and promising for the further development of organophosphorus chemistry. The study of phosphoryl group transfer reactions is important for biological and molecular chemistry, as well as in studying mechanisms of chemical processes involving organophosphorus compounds. New versions of asymmetric electrophilic reactions applicable for the synthesis of enantiopure P-chiral secondary and tertiary phosphines are discussed. Full article
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Scheme 1

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