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New Insights in Diversity Oriented Synthesis
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New Insights in Diversity Oriented Synthesis

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

Deadline for manuscript submissions: closed (30 June 2020) | Viewed by 21942

Special Issue Editor

Prof. Dr. Renata Riva

E-Mail Website
Guest Editor
Department of Pharmacy, Università degli Studi di Genova, Genoa, Italy
Interests: multicomponent reactions; biocatalysis; enantio- and diastereoselective synthesis; green chemistry; fluorescent molecules; diversity oriented synthesis

Special Issue Information

Dear Colleagues,

Diversity oriented synthesis (DOS) is a well established and powerful strategy for the synthesis of highly diversified collections of compounds. DOS requires the availability of efficient synthetic pathways, which should be environmentally benign, short, selective, and atom economical. Stereocontrol can in some instances be an important challenge too. This means that in the future the main question will no longer be "if" but "how efficiently" a molecule (or a collection of similar molecules) can be synthesized. This Special Issue is focussed on two main topics, accordingly with a new philosophy within organic synthesis based on the sustainability: a) the valorization of the starting materials, which should be easily accessible possibly from "bio-based" renewable materials (for example biomass or waste), with the aim to replace in the next future the oil-based chemistry; b) the efficiency of the synthetic methodologies planned to transform the starting materials into the new molecules. In particular catalytic methodologies, including biocatalysis, organocatalysis, photocatalysis, transition metal-based domino or one-pot reactions, can offer an excellent contribute to this goal. Moreover, Multicomponent reactions and green synthetic pathways can support as well the sustainability of the synthtic metodologies, allowing at the same time a diversity oriented approach.

Communications, full papers and short reviews on this topic are really appreciated and welcome.

Prof. Renata Riva
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

  • Organic synthesis
  • Enantioselective synthesis
  • Diastereoselective synthesis
  • Green chemistry
  • Sustainable methodologies
  • Multicomponent reactions
  • Combinatorial Chemistry
  • Diversity oriented synthesis

Published Papers (6 papers)

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Research

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22 pages, 2360 KiB  
Article
Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
by Gabriella Vitali Forconesi, Luca Banfi, Andrea Basso, Chiara Lambruschini, Lisa Moni and Renata Riva
Molecules 2020, 25(14), 3227; https://doi.org/10.3390/molecules25143227 - 15 Jul 2020
Cited by 7 | Viewed by 2684
Abstract
A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further [...] Read more.
A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further cyclizations were performed providing bicyclic polyoxygenated heterocycles. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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11 pages, 1138 KiB  
Article
Organocatalytic Asymmetric Aldol Reaction of Arylglyoxals and Hydroxyacetone: Enantioselective Synthesis of 2,3-Dihydroxy-1,4-diones
by Yu-Hao Zhou, Yu-Zu Zhang, Zhu-Lian Wu, Tian Cai, Wei Wen and Qi-Xiang Guo
Molecules 2020, 25(3), 648; https://doi.org/10.3390/molecules25030648 - 3 Feb 2020
Cited by 5 | Viewed by 3249
Abstract
A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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Figure 1

10 pages, 2816 KiB  
Article
Scalable Preparation of Enantioenriched (S)-5-methylhept-2-en-4-one. Synthesis and Aroma Properties of Achiral Analogues Thereof
by Eva Puchľová, Michal Dendys, Ivan Špánik and Peter Szolcsányi
Molecules 2019, 24(24), 4497; https://doi.org/10.3390/molecules24244497 - 8 Dec 2019
Viewed by 3661
Abstract
(S)-5-Methylhept-2-en-4-one is a key flavour compound in hazelnuts. We have performed its chiral-pool-based chemoenzymatic synthesis with 39% overall yield (73% ee). The four-step aldol-based sequence avoids the use of highly reactive and/or toxic reagents, does not require anhydrous conditions and [...] Read more.
(S)-5-Methylhept-2-en-4-one is a key flavour compound in hazelnuts. We have performed its chiral-pool-based chemoenzymatic synthesis with 39% overall yield (73% ee). The four-step aldol-based sequence avoids the use of highly reactive and/or toxic reagents, does not require anhydrous conditions and uses only distillation as the purification method. Thus, such methodology represents a green and scalable alternative to only two stereoselective approaches towards this natural product known so far. In addition, we have designed and prepared a set of new (di)enones as achiral synthetic analogues of the title compound. The results of their sensory analyses clearly show that relatively minor structural changes of the natural molecule significantly alter its olfactory properties. Thus, simple (poly)methylation completely changes the original hazelnut aroma of (S)-5-methylhept-2-en-4-one and shifts the odour of its analogues to eucalyptus, menthol, camphor, and sweet aroma. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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17 pages, 6350 KiB  
Article
Site Selectivity in Pd-Catalyzed Reactions of α-Diazo-α-(methoxycarbonyl)acetamides: Effects of Catalysts and Substrate Substitution in the Synthesis of Oxindoles and β-Lactams
by Daniel Solé, Ferran Pérez-Janer, Arianna Amenta, M.-Lluïsa Bennasar and Israel Fernández
Molecules 2019, 24(19), 3551; https://doi.org/10.3390/molecules24193551 - 30 Sep 2019
Cited by 6 | Viewed by 2870
Abstract
The Pd-catalyzed intramolecular carbene C–H insertion of α-diazo-α-(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation [...] Read more.
The Pd-catalyzed intramolecular carbene C–H insertion of α-diazo-α-(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation states of Pd and a variety of ligands. It was found that, in the synthesis of oxindoles, ((IMes)Pd(NQ))2 can be used as an alternative to Pd2(dba)3 to catalyze the carbene CArsp2–H insertion, although it was less versatile. On the other hand, it was demonstrated that the Csp3–H insertion leading to β-lactams can be effectively promoted by both Pd(0) and Pd(II) catalysts, the latter being most efficient. Insight into the reaction mechanisms involved in these transformations was provided by DFT calculations. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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Review

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30 pages, 6779 KiB  
Review
Unsymmetrical 1,1-Bisboryl Species: Valuable Building Blocks in Synthesis
by K. Naresh Babu, Fedaa Massarwe, Reddy Rajasekhar Reddy, Nadim Eghbarieh, Manuella Jakob and Ahmad Masarwa
Molecules 2020, 25(4), 959; https://doi.org/10.3390/molecules25040959 - 20 Feb 2020
Cited by 22 | Viewed by 4654
Abstract
Unsymmetrical 1,1-bis(boryl)alkanes and alkenes are organo-bismetallic equivalents, which are synthetically important because they allow for sequential selective transformations of C–B bonds. We reviewed the synthesis and chemical reactivity of 1,1-bis(boryl)alkanes and alkenes to provide information for the synthetic community. In the first part [...] Read more.
Unsymmetrical 1,1-bis(boryl)alkanes and alkenes are organo-bismetallic equivalents, which are synthetically important because they allow for sequential selective transformations of C–B bonds. We reviewed the synthesis and chemical reactivity of 1,1-bis(boryl)alkanes and alkenes to provide information for the synthetic community. In the first part of this review, we disclose the synthesis and chemical reactivity of unsymmetrical 1,1-bisborylalkanes. In the second part, we describe the synthesis and chemical reactivity of unsymmetrical 1,1-bis(boryl)alkenes. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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Scheme 1

18 pages, 6616 KiB  
Review
Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity
by Andrea Menichetti, Francesco Berti and Mauro Pineschi
Molecules 2020, 25(3), 563; https://doi.org/10.3390/molecules25030563 - 28 Jan 2020
Cited by 17 | Viewed by 4314
Abstract
This review focuses upon the use of nitroso Diels–Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of N-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso [...] Read more.
This review focuses upon the use of nitroso Diels–Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of N-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso Diels–Alder reactions encompasses an initial diversification of pathways giving rise to different cycloadducts (direct and inverse). Selective elaborations of these cycloadducts, basically using a reagent-based approach, deliver a discrete number of structurally diverse compounds, including some original heterobicyclic scaffolds and functionalized heterocycles. This forward synthetic planning allowed the individuation of a new biologically active compound based on a novel oxadiaza-bicyclic-[3.3.1]-nonene scaffold which is still under preclinical evaluation. Full article
(This article belongs to the Special Issue New Insights in Diversity Oriented Synthesis)
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