Article
Chemistry, Applied
Jing Huang, Bo Jiang, Xiyuan Zhang, Yanfeng Gao, Xiufang Xu, Zhiwei Miao
Summary: A synthetic strategy for accessing functionalized azabicyclo[3.3.1]alkenones with three tertiary stereocenters has been developed. The method is scalable and the products can be transformed to various eight-membered-ring bridged heterocyclic molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Xiaofeng Zhang, Miao Liu, Desheng Zhan, Manpreet Kaur, Jerry P. Jasinski, Wei Zhang
Summary: A three-component reaction of nonstabilized azomethine ylides derived from alpha-C-H functionalization of tetrahydroisoquinoline has been developed for the regio- and diastereoselective synthesis of spirooxindole-pyrrolidines. This method provides a pot, atom and step economy (PASE) approach for preparing spiro-heterocyclic compounds with biological interest, using readily available cyclic amines, aryl aldehydes, and olefinic oxindoles.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Leijie Zhou, Xue Zhang, Qijun Wang, Min Liu, Wei Wang, Yongjun Wu, Liezhong Chen, Hongchao Guo
Summary: The asymmetric isomerization/annulation cascade reaction of allylamines with allenoates was achieved under the catalysis of chiral phosphine, yielding chiral pyrroline derivatives in high yields with excellent enantioselectivities. The isomerization of N-allylamines to reactive aliphatic imines through a 1,4-proton shift, avoiding the isolation of highly unstable alkyl N-sulfonylimines, is a key step in the reaction.
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Biochemistry & Molecular Biology
Richa Sharma, Lalit Yadav, Ali Adnan Nasim, Ravi Kant Yadav, Rui Hong Chen, Neha Kumari, Fan Ruiqi, Ashoke Sharon, Nawal Kishore Sahu, Sirish Kumar Ippagunta, Paolo Coghi, Vincent Kam Wai Wong, Sandeep Chaudhary
Summary: A series of spirooxindoles based on nitrostyrene were synthesized and shown to have promising in vitro anticancer activity against human lung and liver cancer cell lines.
Article
Chemistry, Multidisciplinary
Malihe Akhavan, Ahmadreza Bekhradnia
Summary: This study presents an efficient and eco-friendly method for the synthesis of a new class of spiro thiazolidines, yielding stereoselective spiro-heterocycle derivatives in high yields. The novel nanocatalyst used in the reaction allows for easy recovery and reuse, while maintaining high diastereoselectivity. The regioselectivity and stereochemistry of the synthesized compounds were established through various spectroscopic techniques.
Article
Chemistry, Organic
Tingting Yan, Kaki Raveendra Babu, Yong Wu, Yang Li, Yuhai Tang, Silong Xu
Summary: A phosphine-catalyzed olefinic cross-coupling reaction between benzyl halides and fumarates has been described, providing trisubstituted alkenes with good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Article
Chemistry, Organic
Linlong Dai, Qiaohong Zhu, Jie Zeng, Yuheng Liu, Guofu Zhong, Xiaoyu Han, Xiaofei Zeng
Summary: The study presents an effective strategy for the synthesis of chiral imidazolidines through catalytic reactions, achieving high yields and enantioselectivities. Additionally, this method can also be applied in the synthesis of chiral vicinal diamines by adjusting the reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Dongqiu Li, Fang Cheng, Yuhai Tang, Jing Li, Yang Li, Jiao Jiao, Silong Xu
Summary: The method described involves a phosphine-catalyzed internal redox [4 + 2] annulation of 1,4-enynoates with electron-deficient alkenes, resulting in the efficient synthesis of highly functionalized cyclohexenes with exclusive regioselectivity and high diastereoselectivity under mild conditions.
Article
Chemistry, Organic
Mark Molnar, Tamas John, Andras Dancso, Miklos Nyerges
Summary: 1,3-Dipolar cycloadditions of different azomethine ylides to 3-nitro-2(1H)-quinolinones resulted in the synthesis of 3a-nitro-4-oxo-1,2,3,3a,5,9b-hexahydropyrrolo[3,4-c]quinoline-4-one derivatives in satisfactory yield, mostly with excellent stereoselectivity. The structure and stereochemistry of the cycloadducts were extensively studied using X-ray and NMR spectroscopy methods.
Review
Chemistry, Multidisciplinary
Mahzad Dehghany, Jennifer M. Schomaker
Summary: Silver offers a cost-effective alternative for asymmetric transformations of alkenes and alkynes, driving selectivity through non-covalent interactions. The reactions enable direct enantioselective transformations of the alkene/alkyne pi bond and functionalization at adjacent C-H bonds.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2021)
Article
Chemistry, Organic
Akshay Subhash Narode, Rai-Shung Liu
Summary: A one-pot synthesis of 5,6-dihydroindolo[2,1-a]isoquinolines from gold-catalyzed annulations between N-(oalkynylphenyl)imines and alpha-diazo esters is described. This cascade reaction involves the attack of the diazo ester at the imine to form cis-aziridine, followed by stereoselective [3 + 3]-annulations with the tethered arylalkyne. This new catalysis has been utilized to prepare a bioactive molecule of 5,6-dihydroindolo[2,1-a]isoquinoline.
Article
Biochemistry & Molecular Biology
Assem Barakat, Matti Haukka, Saied M. Soliman, M. Ali, Abdullah Mohammed Al-Majid, Ayman El-Faham, Luis R. Domingo
Summary: The study successfully synthesized bi-spirooxindole-engrafted rhodanine analogs with excellent stereo-selectivity and high yield through a one-pot multicomponent [3 + 2] cycloaddition reaction. X-ray crystallographic investigations and Hirshfeld calculations revealed the crystal structure and intermolecular interactions, while theoretical study was conducted on the mechanism of the 32CA reaction.
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)
Review
Biochemistry & Molecular Biology
Lei Miao, Yu Zhang, Leaf Huang
Summary: mRNA vaccines have emerged as a promising platform for cancer immunotherapy, showcasing high potency, safe administration, rapid development potentials, and cost-effective manufacturing. However, challenges such as stability, innate immunogenicity, and inefficient in vivo delivery restrict their applications. In addressing these challenges, structural modifications and formulation methods are being researched to enhance the anti-tumor immune response.
Article
Nanoscience & Nanotechnology
Xiaoqi Sun, Yu Zhang, Jiaqian Li, Kyung Soo Park, Kai Han, Xingwu Zhou, Yao Xu, Jutaek Nam, Jin Xu, Xiaoyue Shi, Lei Wei, Yu Leo Lei, James J. Moon
Summary: Metalloimmunotherapy utilizes metal ions to amplify the anti-tumour immune response promoted by STING agonists, forming nanoparticles that effectively deliver STING agonists and achieve remarkable therapeutic efficacy in multiple tumour models. This work highlights the great potential of coordination nanomedicine for metalloimmunotherapy.
NATURE NANOTECHNOLOGY
(2021)
