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Stereogenic Centers II
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Stereogenic Centers II

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2022) | Viewed by 10037

Special Issue Editor

Dr. Alejandro Baeza Carratalá

E-Mail Website
Guest Editor
Organic Chemistry Department and Instituto de Síntesis Orgánica, Universitat d’Alacant, 03690 Alicante, Spain
Interests: asymmetric catalysis; green chemistry; organocatalysis; metal catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The importance of having access to chiral molecules is well known among the scientific community. This is because most of the biological activity that some molecules possess is associated with one of the all-possible enantiomers, which can interact differentially with chiral recognition entities, triggering distinct biochemical responses.

Different methodologies have been developed in the last century, within the frame of so-called asymmetric synthesis, to tackle the challenging task of constructing such chiral compounds, as most of these strategies are based on the construction of stereogenic centers starting from racemic and/or pro-chiral compounds.

Due to the high acceptance and success of the first Stereogenic Centers Issue and the continuous growth of the area, a second edition has been considered to be necessary.

Therefore, this Stereogenic Centers 2 Issue will be focused on gathering the most recent developments for the creation of stereogenic centers in organic molecules. Strategies such as asymmetric synthesis, kinetic resolutions, asymmetric catalysis (metal-, organo-, and bio-catalysis), among others are within the aim of this Special Issue.

Dr. Alejandro Baeza Carratalá
Guest Editor

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Keywords

  • Chirality
  • Stereogenic centers
  • Asymmetric synthesis
  • Asymmetric catalysis
  • Enantiomers

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Published Papers (4 papers)

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Research

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14 pages, 1672 KiB  
Article
3-(((1S,3S)-3-((R)-Hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-oxocyclohexyl)methyl)pentane-2,4-dione: Design and Synthesis of New Stereopure Multi-Target Antidiabetic Agent
by Abdul Sadiq, Mater H. Mahnashi, Umer Rashid, Muhammad Saeed Jan, Mohammed Abdulrahman Alshahrani and Mohammed A. Huneif
Molecules 2022, 27(10), 3265; https://doi.org/10.3390/molecules27103265 - 19 May 2022
Cited by 18 | Viewed by 1900
Abstract
The chiral drug candidates have more effective binding affinities for their specific protein or receptor site for the onset of pharmacological action. Achieving all carbon stereopure compounds is not trivial in chemical synthesis. However, with the development of asymmetric organocatalysis, the synthesis of [...] Read more.
The chiral drug candidates have more effective binding affinities for their specific protein or receptor site for the onset of pharmacological action. Achieving all carbon stereopure compounds is not trivial in chemical synthesis. However, with the development of asymmetric organocatalysis, the synthesis of certain vital chiral drug candidates is now possible. In this research, we have synthesized 3-(((1S,3S)-3-((R)-hydroxy(4-(trifluoromethyl)phenyl)methyl)-4-oxocyclohexyl)methyl)pentane-2,4-dione (S,S,R-5) and have evaluated it potential as multi-target antidiabetic agent. The stereopure compound S,S,R-5 was synthesized with a 99:1 enantiomeric ratio. The synthesized compound gave encouraging results against all in vitro antidiabetic targets, exhibiting IC50 values of 6.28, 4.58, 0.91, and 2.36 in α-glucosidase, α-amylase, PTP1B, and DPPH targets, respectively. The molecular docking shows the binding of the compound in homology models of the respective enzymes. In conclusion, we have synthesized a new chiral molecule (S,S,R-5). The compound proved to be a potential inhibitor of the tested antidiabetic targets. With the observed results and molecular docking, it is evident that S,S,R-5 is a potential multitarget antidiabetic agent. Our study laid the baseline for the animal-based studies of this compound in antidiabetic confirmation. Full article
(This article belongs to the Special Issue Stereogenic Centers II)
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13 pages, 7683 KiB  
Article
Selenium Dihalides Click Chemistry: Highly Efficient Stereoselective Addition to Alkynes and Evaluation of Glutathione Peroxidase-Like Activity of Bis(E-2-halovinyl) Selenides
by Maxim V. Musalov, Vladimir A. Potapov, Arkady A. Maylyan, Alfiya G. Khabibulina, Sergey V. Zinchenko and Svetlana V. Amosova
Molecules 2022, 27(3), 1050; https://doi.org/10.3390/molecules27031050 - 3 Feb 2022
Cited by 5 | Viewed by 1980
Abstract
Highly efficient stereoselective syntheses of novel bis(E-2-chlorovinyl) selenides and bis(E-2-bromovinyl) selenides in quantitative yields by reactions of selenium dichloride and dibromide with alkynes were developed. The reactions proceeded at room temperature as anti-addition giving products exclusively with ( [...] Read more.
Highly efficient stereoselective syntheses of novel bis(E-2-chlorovinyl) selenides and bis(E-2-bromovinyl) selenides in quantitative yields by reactions of selenium dichloride and dibromide with alkynes were developed. The reactions proceeded at room temperature as anti-addition giving products exclusively with (E)-stereochemistry. The glutathione peroxidase-like activity of the obtained products was estimated and compounds with high activity were found. The influence of substituents in the products on their glutathione peroxidase-like activity was discussed. Full article
(This article belongs to the Special Issue Stereogenic Centers II)
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14 pages, 2768 KiB  
Article
Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
by Jade Vaccari, María José González-Soria, Nicholas Carter and Beatriz Maciá
Molecules 2021, 26(15), 4471; https://doi.org/10.3390/molecules26154471 - 24 Jul 2021
Viewed by 2354
Abstract
A catalytic methodology for the enantioselective addition of alkylzirconium reagents to aliphatic aldehydes is reported here. The versatile and readily accessible chiral Ph-BINMOL ligand, in the presence of Ti(OiPr)4 and a zinc salt, facilitates the reaction, which proceeds under mild [...] Read more.
A catalytic methodology for the enantioselective addition of alkylzirconium reagents to aliphatic aldehydes is reported here. The versatile and readily accessible chiral Ph-BINMOL ligand, in the presence of Ti(OiPr)4 and a zinc salt, facilitates the reaction, which proceeds under mild conditions and is compatible with functionalized nucleophiles. The alkylzirconium reagents are conveniently generated in situ by hydrozirconation of alkenes with the Schwartz reagent. This work is a continuation of our previous work on aromatic aldehydes. Full article
(This article belongs to the Special Issue Stereogenic Centers II)
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Review

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21 pages, 6554 KiB  
Review
Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
by Leon Hoppmann and Olga García Mancheño
Molecules 2021, 26(22), 6902; https://doi.org/10.3390/molecules26226902 - 16 Nov 2021
Cited by 9 | Viewed by 2792
Abstract
Mukaiyama aldol, Mannich, and Michael reactions are arguably amongst the most important C–C bond formation processes and enable access to highly relevant building blocks of various natural products. Their vinylogous extensions display equally high potential in the formation of important key intermediates featuring [...] Read more.
Mukaiyama aldol, Mannich, and Michael reactions are arguably amongst the most important C–C bond formation processes and enable access to highly relevant building blocks of various natural products. Their vinylogous extensions display equally high potential in the formation of important key intermediates featuring even higher functionalization possibilities through an additional conjugated C–C double bond. Hence, it is much desired to develop highly selective vinylogous methods in order to enable unconventional, more efficient asymmetric syntheses of biologically active compounds. In this regard, silyl-dienolates were discovered to display high regioselectivities due to their tendency toward γ-additions. The control of the enantio- and diastereoinduction of these processes have been for a long time dominated by transition metal catalysis, but it received serious competition by the application of organocatalytic approaches since the beginning of this century. In this review, the organocatalytic applications of silyl-dienolates in asymmetric vinylogous C–C bond formations are summarized, focusing on their scope, characteristics, and limitations. Full article
(This article belongs to the Special Issue Stereogenic Centers II)
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