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Molecules
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Modern Trends in Catalytic Asymmetric Synthesis
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Modern Trends in Catalytic Asymmetric Synthesis

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

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 2397

Special Issue Editor

Prof. Dr. Plato A. Magriotis

E-Mail Website
Guest Editor
Department of Pharmacy, University of Patras, 26504 Patra, Greece
Interests: synthesis of biologically and pharmacologically relevant molecules; total synthesis of antitumor/antibiotic natural products; new synthetic methodology

Special Issue Information

Dear Colleagues,

The important requirement for approval of a new drug, in case it happens to be chiral, which is that both enantiomers of the drug be studied in detail, has focused the attention of synthetic organic and medicinal chemists on the development of new methods for catalytic asymmetric synthesis of homochiral small organic molecules relevant to drug discovery. Despite the success of chirally modified transition-metal catalysts in asymmetric synthesis, in the form of the Nobel Prize in Chemistry (2001), the field of asymmetric organic synthesis has since been dominated by organocatalysts due to their ability to catalyze a variety of fundamentally important transformations in organic synthesis.

The purpose of this Special Issue is to highlight new catalytic asymmetric processes that have been recently discovered.

Prof. Plato A. Magriotis
Guest Editor

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. Molecules is an international peer-reviewed open access semimonthly 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 2700 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

  • Asymmetric organocatalysis
  • Transition-metal catalyzed organic reactions
  • Carbocycles
  • Saturated N-Heterocycles
  • Β-Lactams
  • Piperazines

Published Papers (1 paper)

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Research

23 pages, 23807 KiB  
Article
A Novel Dual Organocatalyst for the Asymmetric Pinder Reaction and a Mechanistic Proposal Consistent with the Isoinversion Effect Thereof
by Fotini Moschona, Athena Vagena, Veroniki P. Vidali and Gerasimos Rassias
Molecules 2021, 26(21), 6398; https://doi.org/10.3390/molecules26216398 - 22 Oct 2021
Viewed by 1946
Abstract
In general, the Pinder reaction concerns the reaction between an enolisable anhydride and an aldehyde proceeding initially through a Knoevenagel reaction followed by the ring closing process generating lactones with at least two chiral centers. These scaffolds are frequently present in natural products [...] Read more.
In general, the Pinder reaction concerns the reaction between an enolisable anhydride and an aldehyde proceeding initially through a Knoevenagel reaction followed by the ring closing process generating lactones with at least two chiral centers. These scaffolds are frequently present in natural products and synthetic bioactive molecules, hence it has attracted intense interest in organic synthesis and medicinal chemistry, particularly with respect to controlling the diastereo- and enantioselectivity. To the best of our knowledge, there has been only one attempt prior to this work towards the development of a catalytic enantioselective Pinder reaction. In our approach, we designed, synthesized, and tested dual chiral organocatalysts by combining BIMAH amines, (2-(α-(alkyl)methanamine)-1H-benzimidazoles, and a Lewis acid motif, such as squaramides, ureas and thioureas. The optimum catalyst was the derivative of isopropyl BIMAH bearing a bis(3,5-trifluoromethyl) thiourea, which afforded the Pinder products from various aromatic aldehydes with diastereomeric ratio >98:2 and enatioselectivity up to 92 ee%. Interestingly, the enantioselectivity of this catalyzed process is increased at higher concentrations and exhibits an isoinversion effect, namely an inverted "U" shaped dependency with respect to the temperature. Mechanistically, these features, point to a transition state involving an entropy-favored heterodimer interaction between a catalyst/anhydride and a catalyst/aldehyde complex when all other processes leading to this are much faster in comparison above the isoinversion temperature. Full article
(This article belongs to the Special Issue Modern Trends in Catalytic Asymmetric Synthesis)
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