Article
Chemistry, Organic
Ji-Wei Ren, Zhen-Zhen Xie, Lan Zheng, Zhi-Peng Ye, Zhi-Xiong Deng, Qing-Lan Zhao, Jun-An Xiao, Kai Chen, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang
Summary: In this work, an organocatalytic enantioselective ring-reorganization domino sequence was established for the synthesis of pyrrolo[3,4-c]quinolinones with multiple chiral centers. The reaction showed high yields, excellent diastereoselectivities, and high enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Abhisek Midya, Laxman Devidas Khalse, Prasanta Ghorai
Summary: An unprecedented enantioselective organocatalytic spirocyclization strategy was developed by in situ generation of aminoisobenzofulvenes and utilizing iminium-enamine catalysis for a reductive Michael/aldol-condensation/Michael addition cascade. This strategy showed remarkable success in the synthesis of all carbon quaternary spirocycles and demonstrated post-methodological manipulation of the products.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Haiyu Sun, Yicheng He, Wusheng Guo
Summary: This study reports a Pd-catalyzed decarboxylative strategy for the asymmetric construction of spiro[4.5]deca-6,9-dien-8-ones. This approach utilizes modular vinyl methylene cyclic carbonates and p-quinone methides as reaction partners. The reaction can be performed at room temperature and generates CO2 as the sole by-product. The corresponding products feature otherwise synthetically challenging vicinal quaternary carbons, which create great potential for complexity and diversity. The stereochemistry of the reactions is controlled with diastereo- and enantioselectivity being up to >20 : 1 dr and 96 : 4 er.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhi-Hao You, Yan-Kai Liu
Summary: A novel [4+2] cyclization reaction was developed for the asymmetric synthesis of polycyclic compounds containing chromane and spirooxindole moieties. The reaction proceeded via intramolecular E1cB elimination and produced products with good yields (up to 84%) and excellent enantioselectivities (most 98 to >99% ee) using a chiral bifunctional thiourea-tertiary amine catalyst (1-5 mol%).
Article
Chemistry, Multidisciplinary
Michael J. Tilby, Damien F. Dewez, Adrian Hall, Carolina Martinez Lamenca, Michael C. Willis
Summary: In this study, the absolute configuration of sulfur-stereogenic aza-sulfur derivatives was determined using a unique feature of sulfonimidamides. Enantioselective alkylation was achieved by generating prochiral ions from sulfonimidamides with the help of a bis-quaternized phase-transfer catalyst. This demonstrates the potential of using configurationally labile aza-sulfur species in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jun Zhang, Mengmeng Wang, Huiying Wang, Hui Xu, Junjie Chen, Ziqiong Guo, Biao Ma, Shu-Rong Ban, Hui-Xiong Dai
Summary: A strategy of sequential C-H activations of indole was developed to construct novel 2-alkynyl aza-spiro[4,5]indole scaffolds, incorporating both alkyne and spiro-units into indole. The gram-scale synthesis and one-pot, three-step synthesis demonstrated the utility of this protocol. Hybrid conjugates with an oseltamivir derivative provided a powerful tool for constructing a versatile spiroindole-containing library via click chemistry.
CHEMICAL COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Hongwen Mu, Yan Jin, Rongrong Zhao, Liming Wang, Ying Jin
Summary: In this study, bifunctional Takemoto's catalysts were used to catalyze the enantioselective Michael reaction of aminomaleimides with nitroolefins. The resulting products showed good yields and high enantiomeric excess.
Review
Chemistry, Applied
Daniel Gavina, Marcos Escolano, Javier Torres, Gloria Alzuet-Pina, Maria Sanchez-Rosello, Carlos del Pozo
Summary: Substituted and annulated pyrroles containing chiral centers can be accessed through organocatalytic enantioselective Friedel-Crafts alkylation (FCA) reaction. These compounds are interesting due to their natural occurrence and diverse biological activities. In the past two decades, significant synthetic efforts have been made to develop asymmetric transformations involving pyrroles in the FCA reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Marta Meazza, Ramon Rios
Summary: This study describes the first synthesis of 2-alkenylquinolines from 2-allylquinolines and alpha,beta-unsaturated aldehydes. The reaction exhibits high regioselectivity and enantioselectivity, with a broad tolerance of functionalities in both the enal aromatic ring and the quinoline.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Yanfang Han, Long Zhang, Sanzhong Luo
Summary: A highly diastereo- and enantioselective retro-Claisen reaction has been developed using chiral primary amine catalysis. This reaction enables efficient synthesis of chiral beta,beta-diaryl-alpha-branched ketones with excellent stereoselectivities. The reaction proceeds through a tandem sequence involving benzylic C-C bond formation, C-C bond cleavage, and stereospecific enamine protonation. The use of o-quinone methides as diaryl precursors allows for a broad substrate scope, mild reaction conditions, and a high degree of stereocontrol.
Article
Chemistry, Organic
Jing-Xiang Xu, Kai-Ti Chu, Ming-Hsi Chiang, Jeng-Liang Han
Summary: A direct catalytic asymmetric functionalization of 2-methylindoles using organocatalysis was described. An efficient asymmetric allylic alkylation reaction with chiral biscinchona alkaloid catalyst provided functionalized indole derivatives in good yields and enantioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Ana Maria Faisca Phillips, Armando J. L. Pombeiro
Summary: Chiral halogenated substances have significant applications in pharmaceuticals, agrochemicals, and materials, with halogens affecting molecular properties. There are highly-selective halogenating reagents available, allowing functionalization of complex molecules under mild conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Christoph Etling, Giada Tedesco, Markus Kalesse
Summary: This study investigated the different reactivity of trienones under Lewis and Bronsted acids catalysis, resulting in novel Nazarov cyclization tandem reactions terminating oxyallyl cations by ene-type reactions. The bicyclic spiro compounds produced were shown to be useful intermediates for further functionalization. Furthermore, the tandem Nazarov/ene cyclization was found to be preferred over a Nazarov/[3+2] tandem reaction for all substrates, regardless of chain length.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xingfu Wei, Yue Huang, Zahra Karimi, Jingping Qu, Baomin Wang
Summary: A novel DMAP-catalyzed [4+3] spiroannulation reaction was developed for the synthesis of medicinally relevant pyrazolone and azepine nuclei. This reaction yielded diverse spiro[pyrazolone-azepine] products in good to excellent yields (up to 93%) with a wide substrate scope (23 examples) under mild conditions. Gram-scale reactions and product transformations were also conducted, enhancing the diversity of products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)