Article
Chemistry, Multidisciplinary
Ruo-Qing Wang, Chong Shen, Xiang Cheng, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, copper-catalyzed asymmetric propargylic substitution was successfully achieved using salicylaldehyde-derived imine esters and propargylic carbonates, resulting in a wide range of chiral amino acid derivatives containing propargylic groups. The ortho-hydroxy group of the salicylaldehyde-derived imine esters played a crucial role in increasing reactivity and stabilizing the azomethine ylide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Xihao Chang, Jiayin Zhang, Lingzi Peng, Chang Guo
Summary: The study introduces an enantioselective nickel/Lewis acid-catalyzed asymmetric propargylic substitution reaction for the synthesis of structurally diverse natural products from simple achiral materials under mild conditions. The addition of a Lewis acid cocatalyst is crucial for enhancing the efficiency of the transformation and the strategy is powerful for collectively synthesizing seven biologically active compounds.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Wei Wang, Fangqing Zhang, Yangbin Liu, Xiaoming Feng
Summary: In this study, we report a novel method using a bimetallic catalyst for the asymmetric allylation of challenging trisubstituted allylic esters, achieving the construction of vicinal all-carbon quaternary stereocenters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Mayuko Isomura, David A. Petrone, Erick M. Carreira
Summary: A robust catalytic system utilizing chiral Ir-phosphoramidite and La(OTf)(3) enables highly enantioselective alkylation reactions of racemic tertiary alpha-allenyl alcohols with tetrasubstituted silyl ketene acetals. The reaction displays broad functional group tolerance and allows efficient generation of beta-allenyl ester products with excellent enantioselectivity, which can be further upgraded in structural complexity via stereoselective metal-catalyzed functionalization reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Xiang Pu, Qiu-Di Dang, Lei Yang, Xia Zhang, Dawen Niu
Summary: The authors report a doubly-stereoconvergent, Cu/Mg-catalyzed asymmetric propargylic substitution reaction that can selectively construct products with vicinal congested stereocenters. This reaction uses readily available starting materials, environmentally friendly catalysts, and has a broad substrate scope.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Sheng Zuo, Yuan Tao, Zhigang Liu, Ke Zhang, Luyun Zhang, Yingtang Ning, Fen-Er Chen
Summary: This study successfully synthesized highly congested indanone-based spirolactones through copper-catalyzed decarboxylative propargylation, with the key role of DPEN-based ligands. The method tolerated a wide range of functional groups, yielding high diastereo- and enantioselectivities. Mechanistic observations indicated the capability of the new copper complex to enable stereocontrolled addition to copper-allenylidene species.
Article
Chemistry, Multidisciplinary
Andre U. Augustin, Sergio Di Silvio, Ilan Marek
Summary: Here, we demonstrate a method to form acyclic frameworks with two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This approach involves regio-and diastereoselective hydro or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes by adding nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivers the desired compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Wen-Biao Wu, Xin Yu, Jin-Sheng Yu, Xin Wang, Wen-Guang Wang, Jian Zhou
Summary: We report the first highly diastereo- and enantioselective C-C bond-forming reaction of racemic alpha-branched ketones to construct tertiary alcohols with adjacent stereocenters. A highly stereoselective cyanosilylation of racemic ketones is developed, as well as a highly selective kinetic resolution method.
Article
Chemistry, Multidisciplinary
Phillippa Cooper, Andrew G. Dalling, Elliot H. E. Farrar, Timothy P. Aldhous, Simon Grelaud, Eleanor Lester, Lyman J. Feron, Paul D. Kemmitt, Matthew N. Grayson, John F. Bower
Summary: The Ir-catalyzed alkene hydroarylation allows for the efficient synthesis of quaternary benzylic centers, and the structural features of the ligand play a crucial role in the reaction efficiency.
Article
Chemistry, Multidisciplinary
Yang Xi, Chenchen Wang, Qian Zhang, Jingping Qu, Yifeng Chen
Summary: This method efficiently synthesizes the chiral beta-fluoroaminated moiety with high enantioselectivity and exhibits the ability to transform the product into various vicinal benzylic fluoride derivatives with excellent stereo- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xigong Liu, Changyin Zhao, Rongxiu Zhu, Lei Liu
Summary: The study presents a solution for constructing vicinal quaternary carbon stereocenters in acyclic systems, achieving excellent yields and selectivities through asymmetric cross-dehydrogenative coupling reactions. The generality of the approach was further demonstrated, and computational studies elucidated the origins of both diastereo- and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Kieran Nicholson, Yuxuan Peng, Natalia Llopis, Dominic R. Willcox, Gary S. Nichol, Thomas Langer, Alejandro Baeza, Stephen P. Thomas
Summary: This article presents a boron-catalyzed allylation of ketones with allenes, exploring the yield, regioselectivity, and diastereoselectivity of the reaction across functionalized substrates. Furthermore, the reaction is developed for asymmetric ketone allylation using an enantioenriched boron catalyst, achieving good yield, diastereoselectivity, and enantioselectivity. Mechanistic studies support a hydroboration-allylation-transborylation pathway.
Article
Chemistry, Multidisciplinary
Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: In recent years, significant progress has been made in the development of transition metal-catalyzed enantioselective propargylic substitution reactions. However, until now, no successful example with phosphorus-centered nucleophiles has been reported. This study presents the first successful example of ruthenium-catalyzed enantioselective propargylic substitution reactions using propargylic alcohols as substrates and diarylphosphine oxides as phosphorus-centered nucleophiles, providing a new method for preparing chiral phosphorus-containing organic compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Gillian Laidlaw, Vilius Franckevicius
Summary: A palladium-catalyzed decarboxylative asymmetric allylic alkylation has been developed for the synthesis of specific compounds, demonstrating potential for medicinal chemistry applications.
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)
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)