Article
Chemistry, Multidisciplinary
Jan Faehrmann, Gerhard Hilt
Summary: The study presents the acyl nitroso Diels-Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids. By utilizing alternating current electrolysis and optimizing the reaction conditions through Design of Experiments, high purity products were obtained with yields up to 96%, without the need for further purification.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Bhavani Shankar Chinta, Daniel Lee, Thomas R. Hoye
Summary: This study reports a successful reaction of benzynes generated by hexadehydro-Diels-Alder reaction with coumarin to produce phenanthrene derivatives, highlighting the reactivity difference between 2-pyrone and coumarin.
Article
Chemistry, Organic
Shuheng Xu, Linwei Zeng, Sunliang Cui
Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.
Article
Chemistry, Organic
Li-Wen Shen, Zhen-Hua Wang, Yong You, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: An unprecedented (3+1) cyclization of alpha-nitro-sostyrenes, generated in situ from alpha-bromooximes, and N-tosyloxycarbamates was developed, enabling the synthesis of a range of structurally unique and hitherto unexplored 2,3-dihydrodiazete N-oxides in moderate to high yields. The products possess a highly strained four-membered ring structure containing two nitrogen atoms. The synthetic applicability of the products was also demonstrated by many important conversions to diverse nitrogen-containing compounds.
Article
Chemistry, Multidisciplinary
Khaled Youssef, Magali Allain, Thomas Cauchy, Frederic Gohier
Summary: 2-Bromo, 3-bromothiophene, 2,5-dibromothiophene, 3,4-dibromothiophene, and perbrominated thiophene were oxidized under different conditions to form thiophene S,S-dioxide. Depending on the substitution, sulfone was obtained when the hindered thiophene was used. However, monosubstituted thiophenes could not be transformed into sulfone due to the reactivity of the sulfoxide intermediate, which led to dimerization. The structures were confirmed through the obtaining of crystals. The oxidation of 3,4-dibromothiophene could either result in the formation of cycloadduct or the isolation of sulfone, which could further evolve into benzothiophene sulfone.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Jonathan P. Knowles, Hannah G. Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn
Summary: This method transforms simple starting materials into complex tetracyclic products with potential medicinal chemistry applications through a sophisticated chemical catalysis process.
Article
Chemistry, Multidisciplinary
Taehwan Hwang, Joseph P. Tuccinardi, Alexandra A. Beard, Amy C. Jackson, Min J. Jung, John L. Wood
Summary: This article describes the first total syntheses of (+/-)-dracocephalone A (1) and (+/-)-dracocequinones A (4) and B (5). The synthesis was initially envisioned as proceeding through an intramolecular isobenzofuran Diels-Alder reaction but evolved into a Lewis acid-promoted spirocyclization. This highly diastereoselective transformation set the stage for the formation of trans-decalin and a late-stage Suarez oxidation, leading to the desired products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Lei Yu, Wenhai Li, Anyawan Tapdara, Sara Helen Kyne, Mandeep Harode, Rasool Babaahmadi, Alireza Ariafard, Philip Wai Hong Chan
Summary: An efficient chiral gold(I) complex-catalyzed synthetic method for the regio- and enantioselective nitroso-Diels-Alder (NDA) reaction of 1,6-diyne esters with nitrosobenzenes is described. The reaction provides access to a wide range of 3,5,6,8a-tetrahydro-1H-benzo[c][1,2]oxazines as a single regioisomer with high yields and enantiomeric excess values.
Article
Chemistry, Multidisciplinary
Yang Lu, Meng-Meng Xu, Zhi-Mao Zhang, Junliang Zhang, Quan Cai
Summary: The study presented a copper-catalyzed asymmetric IEDDA reaction for the synthesis of six-membered carbocycles, leading to the successful asymmetric total syntheses of cephanolides A and B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Wu-Jingyun Zhou, Xiaoning Yu, Chen Chen, Wei Lan, Gu Zhan, Jin Zhou, Qian Liu, Wei Huang, Qian-Qian Yang
Summary: Here, a series of chiral d-lactam frameworks were synthesized and catalyzed by chiral phosphoric acid (CPA) using two kinds of open-chain aza-dienes and azlactones derived from amino acids. This method shows a broad substrate scope and high efficiency, allowing facile scale-up and conversion to diversely substituted products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A new compound was synthesized successfully in this study by using Yb-(OTf)(3) catalyst to react donor-acceptor cyclopropanes with sulfur-containing 4π components. The reaction showed high yields and moderate to good diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Aurapat Ngamnithiporn, Padon Chuentragool, Poonsakdi Ploypradith, Somsak Ruchirawat
Summary: The development of an intermolecular aza-Diels-Alder (DA) cycloaddition of sultines and imines has been reported. This reaction provides a wide variety of 3-aryl tetrahydroisoquinolines in moderate to excellent yield (up to 89%) by exploiting sultines as o-quinodimethane precursors and aryl imines as dienophiles in the presence of Cu(OTf)(2). The synthetic utility of these products was demonstrated in the preparation of tetracyclic N-heterocycles, including a tetrahydroprotoberberine skeleton.
Article
Polymer Science
Paul van den Tempel, Emiel O. van der Boon, Jozef G. M. Winkelman, Antonina V. Krasnikova, Daniele Parisi, Peter J. Deuss, Francesco Picchioni, Ranjita K. Bose
Summary: The furan-maleimide Diels-Alder chemistry is a useful tool for designing thermo-reversible click networks. In this study, a new reaction in furan-maleimide click networks, called the Double-Diels-Alder reaction (DDA), was reported. This reaction forms extra linkages between Diels-Alder adducts and non-reacted furan groups, resulting in stronger materials but reducing thermal recycling efficiency. The study revealed that the DDA reaction can occur in both intramolecular and intermolecular fashion, and it exhibits reversibility like the regular Diels-Alder reaction. The importance of the DDA reaction in furan-maleimide click networks may be easily overlooked, leading to unexpected reactivity in these systems.
Article
Chemistry, Organic
Dengfu Lu, Lei Chen, Avishek Roy, Zhendong Jin
Summary: 1,3-Dienes derived from (R)-4-t-butyldimethylsilyloxy-2-cyclohexen-1-one react with acyl nitroso dienophiles to form exclusively anti [4 + 2] cycloaddition products. These regio and diastereoselective reactions increase the asymmetric complexity from one chiral center in the starting material to three chiral centers in the products in a single step, providing a powerful approach for the asymmetric synthesis of compounds containing 3,6-dihydro-1,2-oxazine structural feature.
TETRAHEDRON LETTERS
(2023)
