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Molecules
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Cycloaddition Reactions and Their Stereochemistry
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Cycloaddition Reactions and Their Stereochemistry

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

Deadline for manuscript submissions: closed (1 September 2021) | Viewed by 5837

Special Issue Editor

Prof. Dr. Fangrui Zhong

E-Mail Website
Guest Editor
Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), Wuhan 430074, China
Interests: organic synthesis; asymmetric catalysis; synthetic methodologies; artificial enzyme catalysis, sustainable chemistry; biomimetic catalysis

Special Issue Information

Dear Colleagues,

Cycloadditions provide an efficient approach to rapidly building diverse ring systems with molecular complexity. The resulting structural frameworks, including carbocycles and heterocycles, have found wide applications in multiple areas ranging from pharmaceuticals, agricultural chemicals to functional materials. Synthetic methodologies in cycloaddition reactions have been advancing continuously with the innovation of novel powerful catalysts and enabling reagents, as well as the integration of modern energy-input strategies such as photochemical and electrochemical activation. Meanwhile, advances in cycloaddition are accompanied by increasing concerns on the control of stereochemistry such as enantioselectivity and diastereoselectivity. The stereochemical properties of cycloadducts would fundamentally affect their biological profiles or molecular functions. This Special Issue aims to collect recent developments in cycloaddition reactions with concerns regarding stereochemistry. We welcome original research articles and reviews associated with recent achievements in this area.

Prof. Dr. Fangrui Zhong
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

  • Cycloaddition
  • Stereoselectivity
  • Diastereoselectivity
  • Enantioselectivity
  • Asymmetric catalysis
  • Cyclization
  • Annulation

Published Papers (2 papers)

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Research

10 pages, 1429 KiB  
Article
Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
by Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang and Shaoyan Wang
Molecules 2021, 26(10), 2969; https://doi.org/10.3390/molecules26102969 - 17 May 2021
Cited by 8 | Viewed by 2157
Abstract
A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with [...] Read more.
A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method. Full article
(This article belongs to the Special Issue Cycloaddition Reactions and Their Stereochemistry)
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15 pages, 16341 KiB  
Article
Structural Identification between Phthalazine-1,4-Diones and N-Aminophthalimides via Vilsmeier Reaction: Nitrogen Cyclization and Tautomerization Study
by Cheng-Yen Chung, Ching-Chun Tseng, Sin-Min Li, Shuo-En Tsai, Hui-Yi Lin and Fung Fuh Wong
Molecules 2021, 26(10), 2907; https://doi.org/10.3390/molecules26102907 - 13 May 2021
Cited by 6 | Viewed by 3243
Abstract
N-Aminophthalimides and phthalazine 1,4-diones were synthesized from isobenzofuran-1,3-dione, isoindoline-1,3-dione, furo [3,4-b] pyrazine-5,7-dione, or 1H-pyrrolo [3,4-c] pyridine-1,3-dione with monohydrate hydrazine to carry out the 5-exo or 6-endo nitrogen cyclization under the different reaction conditions. Based on the [...] Read more.
N-Aminophthalimides and phthalazine 1,4-diones were synthesized from isobenzofuran-1,3-dione, isoindoline-1,3-dione, furo [3,4-b] pyrazine-5,7-dione, or 1H-pyrrolo [3,4-c] pyridine-1,3-dione with monohydrate hydrazine to carry out the 5-exo or 6-endo nitrogen cyclization under the different reaction conditions. Based on the control experimental results, 6-endo thermodynamic hydrohydrazination and kinetical 5-exo cyclization reactions were individually selective formation. Subsequently, Vilsmeier amidination derivatization was successfully developed to probe the structural divergence between N-aminophthalimide 2 and phthalazine 1,4-dione 3. On the other hand, the best tautomerization of N-aminophthalimide to diazinone was also determined under acetic acid mediated solution. Full article
(This article belongs to the Special Issue Cycloaddition Reactions and Their Stereochemistry)
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