Article
Chemistry, Organic
Manickam Bakthadoss, Mohammad Mushaf, Vishal Agarwal, Tadiparthi Thirupathi Reddy, Duddu S. Sharada
Summary: An efficient protocol for the synthesis of tricyclic pyrrolidinochromenes has been developed via an intramolecular 1,3-dipolar cycloaddition. The reaction is highly regio- and diastereoselective, providing potentially bioactive compounds with two rings and four stereogenic centers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kan-Lei Ji, Shu-Fan He, Dong-Dong Xu, Wen-Xin He, Jian-Feng Zheng, Pei-Qiang Huang
Summary: A concise asymmetric total synthesis of (-)-quinocarcin has been achieved through high step economy using commercially available starting materials. The key chiral pyrrolidine intermediate with three stereocenters was prepared via a catalytic enantioselective reductive 1,3-dipolar cycloaddition reaction. This synthesis also involved a Rh-III-catalyzed C-H activation/cyclization and a tandem diastereoselective hydrogenation/cyclization to construct the tetrahydroisoquinoline-pyrrolidine tetracyclic core unit of quinocarcin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Asmaa Belabbes, Veronica Selva, Francisco Foubelo, M. De Gracia Retamosa, Jose M. Sansano
Summary: The synthesis of complex spiro{pyrrolidine-3,1'-pyrrolo[3,4-c]pyrrole} skeleton under mild conditions is presented, with the order of addition of a primary amine and two equivalents of corresponding maleimide being crucial for high yields. The mechanism was studied by simple tests, revealing the Michael type addition of the amine onto the maleimide as a key step. Interesting scaffold hybrids were prepared through sequential addition of two different maleimides, and a more intriguing architecture was obtained through a metathesis reaction between allylic residues in the molecule precursor.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Caiyun Yang, Sirou Hu, Xinhui Pan, Ke Yang, Ke Zhang, Qingguang Liu, Xiaobing Xin, Jie Li, Jinhui Wang, Xiaoda Yang
Summary: This article presents a detailed method for synthesizing 3-benzoxoxazoline using alkenes (alkynes) and various α-nitroketones in the presence of p-TsOH. The reaction covers a wide range of alkenes, including different alkenes and alkynes. This reaction offers a convenient and efficient approach for synthesizing 3-benzoylisoxazolines.
Article
Biochemistry & Molecular Biology
Denisa Dumitrescu, Sergiu Shova, Constantin Draghici, Marcel Mirel Popa, Florea Dumitrascu
Summary: 3-Arylsydnones bearing fluorine and bromine atoms on the benzene ring were synthesized and used in the synthesis of 1-(2-fluorophenyl)pyrazoles by 1,3-dipolar cycloaddition reaction. The sydnones were characterized as reaction intermediates using single crystal X-ray diffraction analysis, revealing halogen bonding as an important interaction in modeling the crystal structure.
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Biochemistry & Molecular Biology
Dmitriy D. Karcev, Mariia M. Efremova, Alexander P. Molchanov, Nikolai Rostovskii, Mariya A. Kryukova, Alexander S. Bunev, Dmitry A. Khochenkov
Summary: In this study, new highly functionalized 5-spiroisoxazolidines were synthesized through the 1,3-dipolar cycloaddition reaction, which showed good selectivity. The reversibility of these reactions allows for controlling the diastereoselectivity of cycloaddition. Additionally, the reduction reaction of the obtained adducts provides 1,3-aminoalcohols or spirolactones.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
You-Gui Li, Wei-Ke Chen, You-Qiang Guo, Zhang Zhu, Jing-Jing Cao, Zhen-Yu Wang, Xiang Wu
Summary: A new method for synthesizing hexahydropyrrolo-isoquinolines through 1,3-dipolar cycloaddition is described. This method involves the reaction of cinnamaldehydes with azomethine ylides generated from cinnamaldehydes and tetrahydroisoquinolines. The key features of this method are easily available substrates, good functional group tolerance, and mild reaction conditions. The relative configurations of the products are confirmed by X-ray analysis, and a plausible mechanism is proposed. A gram-scale experiment and some chemical transformations were conducted to demonstrate the synthetic utility of this approach. (c) 2023 Elsevier Ltd. All rights reserved.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Johannes N. Lamhauge, David A. McLeod, Casper L. Barlose, Gwyndaf A. Oliver, Laura Viborg, Tobias Warburg, Karl Anker Jorgensen
Summary: This article reports a method for the synthesis of tropane derivatives using (5+2) cycloaddition reactions, with excellent stereo selectivity and yield. The mechanism and conditions of this reaction were determined through a series of experiments.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang, Shaoyan Wang
Summary: The [3 + 2] 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved, resulting in a range of tetrahydroisoquinoline derivatives with good diastereoselectivities and enantioselectivities. The absolute configuration of the product was determined using quantum electronic circular dichroism calculation and ECD spectrum method.
Article
Chemistry, Organic
Hao Zeng, Xiaojie Fang, Zhiyi Yang, Chuanle Zhu, Huanfeng Jiang
Summary: A general and practical method for the synthesis of 5-trifluoromethylpyrazoles has been reported, using a coupling reaction between hydrazonyl chlorides and the industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP). This catalyst-free [3 + 2] cycloaddition shows high regioselectivity, mild conditions, high yields, scalability, broad substrate scope, and tolerance for various functional groups, with application in synthesizing key intermediates for an active agonist of sphingosine 1-phosphate receptor.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Houda Gazzeh, Fadwa Rouatbi, Sami Chniti, Moheddine Askri, Michael Knorr, Carsten Strohmann, Christopher Golz, Al Mokhtar Lamsabhi
Summary: The mechanism of a three-component one-pot cycloaddition reaction was studied using both theoretical and experimental methods. The reactivity difference between the unsymmetrical exocyclic dienones was analyzed to explain the observed regio- and stereoselectivity, and the results were confirmed by calculations. The reaction proceeded under kinetic control and showed chemoselectivity, producing two highly diastereomerically enriched compounds. The intermolecular hydrogen bonding and optical properties of the products were also investigated.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Yasunori Toda, Kayo Sato, Kensuke Sato, Kazuma Nagasaki, Hirotaka Nakajima, Ayaka Kikuchi, Kimiya Sukegawa, Hiroyuki Suga
Summary: This paper reports on the chiral binaphthyldiimine-Ni(II)-catalyzed asymmetric 1,3-dipolar cycloaddition reactions between acyclic carbonyl ylides generated from donor-acceptor oxiranes and aldehydes. Both aromatic and aliphatic aldehydes can be used as dipolarophiles, providing cis-1,3-dioxolanes with high diastereo- and enantioselectivities. Mechanistic studies suggest that a monomeric chiral Ni(II) complex acts as the active species for the cycloaddition, and the high levels of asymmetric induction can be explained by a concerted-asynchronous endo Si-face approach of the aldehyde.
Article
Chemistry, Applied
Magesh Sampath, Sembian Ruso Jayaraman, Vishnuvardhan Reddy Eda, Rajendar Potham, Rajeev Rehani Budhdev, Saikat Sen, Rakeshwar Bandichhor, Srinivas Oruganti
Summary: An efficient and elegant enantioselective synthesis of the key chiral pyrrolidine fragment for Upadacitinib (ABT-494) was described using Oppolzer's chiral sultam-directed asymmetric 1,3 dipolar cycloaddition. The method provided the desired level of diastereoselectivity and enantioselectivity in the construction of the 3,4-syn substituted pyrrolidine moiety.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Multidisciplinary
Tobias Sandmeier, Erick M. Carreira
Summary: The study introduces the enantio- and chemoselective N-allylation of oximes, yielding cyclic nitrones and enantioenriched aliphatic allylic alcohols through intramolecular kinetic resolution. The method stands out for its ability to utilize E/Z-isomeric oxime mixtures convergently and high functional group tolerance, showcasing its synthetic utility with the formal synthesis of (+)-halichlorine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Business
Zhe Zhang, Vanessa M. Patrick
Summary: This research demonstrates that the use of brand nicknames in user-generated content enhances perceived information authenticity and leads to positive downstream consequences. However, the effect is attenuated when brand nicknames are used in firm-generated content.
JOURNAL OF MARKETING
(2021)
Article
Business
Shaobo (Kevin) Li, Zhe Zhang, Yue Liu, Sharon Ng
Summary: This research explores the impact of individuals' distance from the COVID-19 epicenter on consumers' risk perception and behaviors, finding that those closer to the epicenter perceive lower risk and engage in less irrational consumption behaviors. The distance proximity effect is mediated by consumers' perception of uncertainty and moderated by individuals' risk aversion tendency.
PSYCHOLOGY & MARKETING
(2021)
Article
Business
Ruiyang Hong, Zhe Zhang, Chun Zhang, Zuohao Hu
Summary: This study aims to investigate hybrid brand positioning strategies for emerging market brands, and finds that highlighting brand COO and de-emphasizing brand globalness is the best positioning strategy.
INTERNATIONAL MARKETING REVIEW
(2023)
