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Recent Trends in Stereoselective Synthesis and Chiral Catalysis
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Recent Trends in Stereoselective Synthesis and Chiral Catalysis

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: closed (20 December 2024) | Viewed by 5915

Special Issue Editor

Prof. Dr. Zsolt Szakonyi

E-Mail Website
Guest Editor
Institute of Pharmaceutical Chemistry, University of Szeged (SZTE), Szeged, Hungary
Interests: beta-amino acids; aminodiols; heterocyclic chemistry; drug design and synthesis; chiral catalysts; terpenoids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Since the end of the 18th century, it has been well known that chirality is fundamental to the natural world around us because, at the molecular level, the highly asymmetric landscape of many fundamental components of plants and animals, such as enzymes, proteins, polysaccharides, and nucleic acids, can be found existing in their chirally pure forms. Because of the chiral nature of biomolecules, their activity can be successfully modified or even blocked by synthetic chiral agents. Therefore, enantioselective syntheses of known or new biologically active molecules, the development of efficient chiral catalysts, or new separation technics for the successful separation of enantiomers are very intensively researched areas within organic chemistry.

The main aim of the present Special Issue is to collect the results of fundamental studies and applications in a multidisciplinary research area that enrols chiral compounds. It will bring together novel, unique, and innovative approaches in the fields of enantioselective organic synthesis, stereoselective transformations, as well as asymmetric organocatalysis and chiral recognition studies using chiral sources, including results of pharmacological studies. Both original research papers and reviews in these fields are welcome.

Prof. Dr. Zsolt Szakonyi
Guest Editor

Manuscript Submission Information

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Keywords

  • chiral synthesis
  • natural source
  • stereoselective
  • bioactive compounds
  • organocatalysis
  • chiral pools
  • biomolecules
  • pharmacological activity
  • chiral building blocks

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Published Papers (5 papers)

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Research

22 pages, 4325 KiB  
Article
VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality
by Zoltán Czenke, Attila Mándi, Sándor Balázs Király, Attila Kiss-Szikszai, Anita Kónya-Ábrahám, Anna Kurucz-Szabados, Krisztián Cserepes, Attila Bényei, Changsheng Zhang, Máté Kicsák and Tibor Kurtán
Int. J. Mol. Sci. 2024, 25(17), 9657; https://doi.org/10.3390/ijms25179657 - 6 Sep 2024
Viewed by 817
Abstract
Optically active heterodimeric 5,5′-linked bis-isochromans, containing a stereogenic ortho-trisubstituted biaryl axis and up to four chirality centers, were synthesized stereoselectively by using a Suzuki–Miyaura biaryl coupling reaction of optically active isochroman and 1-arylpropan-2-ol derivatives, providing the first access to synthetic biaryl-type [...] Read more.
Optically active heterodimeric 5,5′-linked bis-isochromans, containing a stereogenic ortho-trisubstituted biaryl axis and up to four chirality centers, were synthesized stereoselectively by using a Suzuki–Miyaura biaryl coupling reaction of optically active isochroman and 1-arylpropan-2-ol derivatives, providing the first access to synthetic biaryl-type isochroman dimers. Enantiomeric pairs and stereoisomers up to seven derivatives were prepared with four different substitution patterns, which enabled us to test how OR, ECD, and VCD measurements and DFT calculations can be used to determine parallel central and axial chirality elements in three isolated blocks of chirality. In contrast to natural penicisteckins A–D and related biaryls, the ECD spectra and OR data of (aS) and (aR) atropodiastereomers did not reflect the opposite axial chirality, but they were characteristic of the central chirality. The atropodiastereomers showed consistently near-mirror-image VCD curves, allowing the determination of axial chirality with the aid of DFT calculation or by comparison of characteristic VCD transitions. Full article
(This article belongs to the Special Issue Recent Trends in Stereoselective Synthesis and Chiral Catalysis)
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14 pages, 1893 KiB  
Article
Synthesis of Natural and Sugar-Modified Nucleosides Using the Iodine/Triethylsilane System as N-Glycosidation Promoter
by Martina Cimafonte, Anna Esposito, Maria De Fenza, Francesco Zaccaria, Daniele D’Alonzo and Annalisa Guaragna
Int. J. Mol. Sci. 2024, 25(16), 9030; https://doi.org/10.3390/ijms25169030 - 20 Aug 2024
Viewed by 677
Abstract
The reagent system based on the combined use of Et3SiH/I2 acts as an efficient N-glycosidation promoter for the synthesis of natural and sugar-modified nucleosides. An analysis of reaction stereoselectivity in the absence of C2-positioned stereodirecting groups revealed high selectivity [...] Read more.
The reagent system based on the combined use of Et3SiH/I2 acts as an efficient N-glycosidation promoter for the synthesis of natural and sugar-modified nucleosides. An analysis of reaction stereoselectivity in the absence of C2-positioned stereodirecting groups revealed high selectivity with six-membered substrates, depending on the nucleophilic character of the nucleobase or based on anomerization reactions. The synthetic utility of the Et3SiH/I2-mediated N-glycosidation reaction was highlighted by its use in the synthesis of the investigational drug apricitabine. Full article
(This article belongs to the Special Issue Recent Trends in Stereoselective Synthesis and Chiral Catalysis)
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Scheme 1

25 pages, 4837 KiB  
Article
Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers
by Márton Benedek Háznagy, Antal Csámpai, Imre Ugrai, Barnabás Molnár, Matti Haukka and Zsolt Szakonyi
Int. J. Mol. Sci. 2024, 25(8), 4325; https://doi.org/10.3390/ijms25084325 - 13 Apr 2024
Viewed by 1300
Abstract
A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with [...] Read more.
A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (−)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues. Full article
(This article belongs to the Special Issue Recent Trends in Stereoselective Synthesis and Chiral Catalysis)
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Figure 1

11 pages, 2389 KiB  
Article
Synthesis of Enantiopure (S)-Atenolol by Utilization of Lipase-Catalyzed Kinetic Resolution of a Key Intermediate
by Mari Bergan Hansen, Anna Lifen Tennfjord, Fredrik Heen Blindheim, Lucas Hugo Yvan Bocquin and Elisabeth Egholm Jacobsen
Int. J. Mol. Sci. 2024, 25(6), 3497; https://doi.org/10.3390/ijms25063497 - 20 Mar 2024
Cited by 1 | Viewed by 1079
Abstract
(S)-Atenolol ((S)-2-(4-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide) has been synthesized in >99% enantiomeric excess (ee) with the use of Candida antarctica lipase B from Syncozymes (Shanghai, China), in a kinetic resolution of the corresponding racemic chlorohydrin. A catalytic amount of base was [...] Read more.
(S)-Atenolol ((S)-2-(4-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide) has been synthesized in >99% enantiomeric excess (ee) with the use of Candida antarctica lipase B from Syncozymes (Shanghai, China), in a kinetic resolution of the corresponding racemic chlorohydrin. A catalytic amount of base was used in deprotonation of the phenol building block. The enantiopurity of the chlorohydrin building block remained unchanged upon subsequent amination to yield the final drug. All four steps in the synthesis protocol have been optimized compared to previously reported methods, which makes this new protocol more sustainable and in accordance with green chemistry principles. The overall yield of (S)-atenolol was 9.9%, which will be further optimized. Full article
(This article belongs to the Special Issue Recent Trends in Stereoselective Synthesis and Chiral Catalysis)
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Figure 1

11 pages, 6146 KiB  
Communication
The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis
by Elena Sh. Saigitbatalova, Liliya Z. Latypova, Almaz A. Zagidullin, Almira R. Kurbangalieva and Ilya D. Gridnev
Int. J. Mol. Sci. 2023, 24(23), 17048; https://doi.org/10.3390/ijms242317048 - 1 Dec 2023
Cited by 1 | Viewed by 1178
Abstract
A previously unknown reduction of carbonyl compounds with dicyclopentylzinc is reported. Aldehydes react in mild conditions yielding corresponding primary alcohols and cyclopentene. Although cyclohexanone and acetophenone are inert to dicyclopentylzinc, a variety of heterocyclic ketones reacted readily, yielding reasonable to high yields of [...] Read more.
A previously unknown reduction of carbonyl compounds with dicyclopentylzinc is reported. Aldehydes react in mild conditions yielding corresponding primary alcohols and cyclopentene. Although cyclohexanone and acetophenone are inert to dicyclopentylzinc, a variety of heterocyclic ketones reacted readily, yielding reasonable to high yields of corresponding secondary alcohols. When the reaction was catalyzed with (–)-(1R,2S)-ephedrine, 3-acetylpyridine (10) resulted in a high yield of (S)-1-(pyridin-3-yl)ethanol (19) with >99% ee. 5-Acetyl-2-bromopyridine (11) also provided the corresponding optically active alcohol 20, albeit with a much lower optical yield. When 10% of 19 with 92% ee was used as an autocatalyst, 55% yield of the same compound was obtained, with 95% ee and 96% ee in two independent experiments. A three-stage reaction sequence starting from “no chirality” reaction yielded 19 with 6% ee. Thus, amplifying autocatalysis was detected in the reaction of ketone 10 with dicylopentylzinc. Full article
(This article belongs to the Special Issue Recent Trends in Stereoselective Synthesis and Chiral Catalysis)
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