Article
Chemistry, Organic
Patricia B. Momo, Eduardo F. Mizobuchi, Radell Echemendia, Isabel Baddeley, Matthew N. Grayson, Antonio C. B. Burtoloso
Summary: Enantioselective sulfa-Michael additions to alpha,beta-unsaturated diazocarbonyl compounds have been developed using quinine-derived squaramide as the catalyst. This method allows the formation of C-S bonds with high stereoselectivity for alkyl and aryl thiols. The synthesis of 22 examples showed enantiomeric ratios up to 97:3 and reaction yields up to 94%. Density functional theory (DFT) calculations were used to determine the mechanism and origins of enantioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Shuhui Li, Xiaoxuan Li, Hui Yao, Mengting Tan, Dan Xu, Nianyu Huang, Nengzhong Wang
Summary: Straight-chain omega-amino-alpha, beta-unsaturated carbonyl compounds are versatile organic synthons with important applications in organocatalysis. This review discusses the recent applications of these synthons in covalent catalysis, non-covalent catalysis, and bifunctional catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Multidisciplinary
Tapaswini Das, Seetaram Mohapatra, Nilima P. Mishra, Sabita Nayak, Bishnu P. Raiguru
Summary: The recent advancements in organocatalytic Michael addition reactions to alpha, beta-unsaturated nitroolefins have been discussed, highlighting the rapid innovations made possible by newly developed chiral organocatalysts and the essential role of nitroolefins as well-known Michael acceptors providing structurally necessary nitro-functionalized frameworks.
Article
Chemistry, Organic
Shunya Morita, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: In DMSO, a catalytic amount of Barton's base (BTMG) effectively catalyzed intermolecular three-component reactions, forming new three-component addition products with the reaction of α, β-unsaturated esters, aldehydes, and carbon-, sulfur-, or nitrogen-pronucleophiles. The mechanism involves the formation of anionic nucleophiles from pronucleophiles catalyzed by BTMG, followed by intermolecular aldol reactions of transient ester enolates.
Article
Chemistry, Organic
Yong-Sen Shi, Jian-Feng Liu, Xiao-Lan Wu, De-Hong Ke, Sheng Xu
Summary: In this study, a new domino reaction was introduced for the synthesis of (E)-alpha-hydroxyethyl-alpha,beta-unsaturated aldehydes using tetrahydrofuran (THF) as carbonyl block. The method is simple and efficient, with notable advantages of widespread availability of substrates.
TETRAHEDRON LETTERS
(2021)
Review
Chemistry, Multidisciplinary
Cheng Niu, Da-Ming Du
Summary: This review highlights the recent advancements in sulfa-Michael addition-triggered cascade reactions for the stereoselective synthesis of sulfur-containing compounds. It discusses various types of reactions, including sulfa-Michael/aldol, sulfa-Michael/Henry, sulfa-Michael/Michael, sulfa-Michael/Mannich and some sulfa-Michael triggered multi-step processes. The review also introduces reaction mechanisms and derivatization experiments.
Review
Chemistry, Multidisciplinary
Yin Xu, Tong-Yi Zhai, Zhou Xu, Long-Wu Ye
Summary: Desymmetrization is a practical and efficient strategy in synthetic chemistry for assembling valuable molecular complexity. Organocatalysis has become a powerful tool in asymmetric catalysis, and recent progress has been made in combining organocatalysis with desymmetrization.
TRENDS IN CHEMISTRY
(2022)
Letter
Chemistry, Organic
Marta Romaniszyn, Anna Skrzynska, Joanna Dybowska, Lukasz Albrecht
Summary: A novel organocatalytic reaction cascade has been described for the stereocontrolled functionalization of cyanocoumarins, producing biologically active coumarin and delta-lactone-fused products.
Article
Chemistry, Multidisciplinary
Ingolf Harden, Frank Neese, Giovanni Bistoni
Summary: The formation of Bronsted acid aggregates in asymmetric organocatalytic reactions has a significant impact on the stereo-controlling factors of the transformations. This study uses high-level quantum mechanical calculations to investigate the influence of catalyst structure and reaction conditions on the spontaneity of the aggregation process, shedding light on its importance.
Article
Chemistry, Multidisciplinary
Ingolf Harden, Frank Neese, Giovanni Bistoni
Summary: This study investigates the aggregation process of chiral organocatalysts derived from phosphoric acids using high-level quantum mechanical calculations. The results show that the formation of catalyst dimers is possible and the aggregation process can significantly affect the stereo-controlling factors, reaction kinetics, and selectivity of the transformations.
Article
Chemistry, Applied
Yabo Deng, Shuo Sun, Yuqiang Wang, Pengfeng Jia, Wenguang Li, Kairong Wang, Wenjin Yan
Summary: A novel domino reaction has been disclosed utilizing quinidine-derived ammonium salts as a phase transfer catalyst, facilitating the efficient synthesis of a range of CF2H-containing spirofindoline-3,3'-thiophenels under mild conditions. The reaction resulted in high yields, excellent diastereoselectivities, and good enantioselectivities in short reaction times.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Daniel Rozsar, Michele Formica, Ken Yamazaki, Trevor A. Hamlin, Darren J. Dixon
Summary: This paper describes a metal-free catalytic intermolecular enantioselective Michael addition to unactivated alpha,beta-unsaturated amides. Consistently high enantiomeric excesses and yields were obtained under mild reaction conditions, using a novel squaramide-based bifunctional iminophosphorane catalyst. Computational analysis revealed the origin of the high enantiofacial selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Jason Fang, Laura E. Turner, Michelle C. Y. Chang
Summary: Fluorine is a critical element in designing bioactive compounds, but the synthesis of stereogenic tertiary fluorides is challenging and limited to a few approved drugs. In this study, the aldol reaction of fluorinated donors catalyzed by HpcH and engineered variants was found to generate enantiopure secondary and tertiary fluorides. This method not only represents the first synthesis of tertiary fluorides via biocatalysis but also increases the diversity of fluorinated building blocks and enables the synthesis of fluorinated drug analogs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Rayhan G. Biswas, Sumit K. Ray, Rajshekhar A. Unhale, Vinod K. Singh
Summary: A bifunctional urea catalyzed cascade reaction of 5-alkenyl thiazolones and monofluorinated beta-diketones, derived from quinine, has been developed, yielding fluorine containing 4-acyloxy thiazoles with high yields and good diastereo- and excellent enantioselectivities. Synthetic transformations, including the synthesis of 4-hydroxy thiazoles, have been successfully demonstrated.
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)
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)