Article
Chemistry, Multidisciplinary
Jun Zhang, Xuefeng Wang, Peiqi Wang, Jiayuan Fang, Shaoyu Li, Jie Wu
Summary: In this study, an enantioselective copper/bisoxazoline catalyzed oxysulfonylation of alkenes was reported, leading to the synthesis of isoxazolinyl-containing beta-chiral sulfones bearing quaternary carbon stereocenters with high yields and selectivity. The advantage and irreplaceability of this catalytic system were demonstrated by achieving transformations that were not possible with the previously reported sulfonyl chloride system.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ming-Yao Huang, Yu-Tao Zhao, Cheng-Da Zhang, Shou-Fei Zhu
Summary: This study reports a highly selective method for the B-H bond insertion reactions of alpha-silylcarbenes generated from 1-silylcyclopropenes using a chiral copper(I)/bisoxazoline catalyst. The method allows for the construction of chiral gamma,gamma-disubstituted allylic gem-silylboranes, which cannot be prepared using any other known methods. The newly developed products are versatile allylic bimetallic reagents with high stability and great synthetic potential for the construction of complex molecules with continuous chiral centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Miquel Costas
Summary: The selective oxidation of aliphatic C-H bonds is still an unsolved problem in organic synthesis, but complexes with linear tetraazadentate ligands have proven to be structurally versatile and instrumental in designing new C-H oxidation reactions.
Article
Chemistry, Multidisciplinary
David Savary, Olivier Baudoin
Summary: C-H activation-based ring-forming methods are powerful for constructing complex molecular structures, especially useful for synthesizing chiral polycyclic aromatic hydrocarbons and other important organic electronic materials. A new enantioselective synthesis method using Pd-catalyzed C(sp(2))-H arylation protocol has been described, delivering diverse polycyclic compounds with high yield and good to excellent enantioselectivity, with investigation into their chiroptical properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Kai Dong, Chen Xu, Jinsong Ren, Xiaogang Qu
Summary: Nanozymes, which combine enzymatic activity and nanomaterials, have gained significant attention. However, substrate selectivity is often overlooked in the development of nanozymes. This Mini-review provides an overview of recent advances in synthesizing chiral nanozymes and their enantioselective biological catalysis, along with current challenges, potential solutions, and future trends.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chen Li, Bin Chen, Xiaodong Ma, Xueling Mo, Guozhu Zhang
Summary: A catalytic asymmetric alkylation of azoles with secondary 1-arylalkyl bromides through direct C-H functionalization was reported. The reaction, under blue-light photoexcitation, showed good reactivity and high stereoselectivity, providing an efficient strategy for the construction of chiral alkyl azoles at low temperature. The reactions are compatible with a wide range of azoles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Lianqian Wu, Zhihan Zhang, Dunqi Wu, Fei Wang, Pinhong Chen, Zhenyang Lin, Guosheng Liu
Summary: An unprecedented highly enantioselective radical azidation of acrylamides catalyzed by 1 mol% of a copper catalyst is reported. The use of a specific ligand is crucial for generating a monomeric Cu-II azide species for this highly enantioselective transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jing Guo, Ying Xie, Ze-Min Lai, Jiang Weng, Albert S. C. Chan, Gui Lu
Summary: The potential of electron donor-acceptor (EDA) complex photochemistry in visible light-induced photocatalyst-free radical reactions has recently been recognized. However, designing catalytic asymmetric reactions driven by EDA complexes remains challenging. Existing examples are limited to single activation modes with aminocatalysts or phase-transfer catalysts. In this study, chiral bifunctional hydrogen-bonding catalysis is demonstrated to enable the asymmetric reaction of an EDA complex via dual activation modes, resulting in the formation of vicinal tertiary stereocenters at the beta,gamma-positions of pyridines with high yields and good enantio- and diastereoselectivities.
Article
Chemistry, Physical
Jacob Werth, Matthew S. Sigman
Summary: The study utilizes multivariate linear regression analysis to investigate different categories of BOX catalyzed reactions, developing predictive models for various asymmetric catalytic reactions including Cu, Ni, Fe, Mg, and Pd complexes, and reveals the structural requirements necessary for high selectivity through analysis of diverse organometallic intermediates.
Article
Chemistry, Organic
Kotone Murakami, Kana Sakamoto, Takahiro Nishimura
Summary: Chiral phosphoramidite-olefin hybrid ligands were effective in the iridium-catalyzed asymmetric alkylation of N-arylbenzamides with vinyl ethers. The reaction yield was high, with high branch selectivity and enantioselectivity.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Multidisciplinary
Remi Jouhannet, Samuel Dagorne, Aurelien Blanc, Pierre de Fremont
Summary: This article summarizes the synthesis and applications of well-defined gold(III) complexes reported over the last fifteen years, exploring the applications of gold catalysis in organic chemistry and the potential of gold(III) complexes in pharmacology.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Mengyu Xue, Jinfeng Cui, Xiaotao Zhu, Fei Wang, Daqi Lv, Zaicheng Nie, Yajun Li, Hongli Bao
Summary: Chiral gamma-butyrolactones with two non-vicinal carbon stereocenters were efficiently synthesized using a well-designed copper/PyBox catalytic system. This method overcame the intrinsic stereoinduction of the close chirality center and achieved good to excellent enantioselectivities for both diastereoisomers. Additionally, the method selectively provided a single diastereoisomer through epimerization effect and synthesized all four diastereoisomers using opposite chiral ligands L2 and L2'. The obtained chiral gamma-butyrolactones can be further transformed into acyclic or cyclic molecules with two non-vicinal carbon stereocenters. Mechanistic studies revealed a linear relationship in this radical reaction, requiring less loading of ligand compared to the copper catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Guanghao Huang, Regis Guillot, Cyrille Kouklovsky, Boris Maryasin, Aurelien de la Torre
Summary: A broadly applicable diastereo- and enantioselective inverse-electron-demand Diels-Alder reaction of 2-pyrones and acyclic enol ethers is reported, leading to the synthesis of bridged bicyclic lactones with high yields and enantioselectivities using a copper(II)-BOX catalytic system. Mechanistic studies suggest a stepwise mechanism, and the synthetic potential of the bridged bicyclic lactones is demonstrated through the enantioselective synthesis of polyfunctional cyclohexenes and cyclohexadienes, as well as a carbasugar unit.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Linghua Wang, Tao Li, Saima Perveen, Shuai Zhang, Xicheng Wang, Yizhao Ouyang, Pengfei Li
Summary: A nickel-catalyzed general, efficient, and highly enantioselective carboxylation reaction of racemic benzylic (pseudo)halides has been developed, utilizing atmospheric CO2 under mild conditions. A unique chiral 2,2'-bipyridine ligand enabled both high reactivity and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Raja K. K. Rit, Hongyi Li, Stephen P. P. Argent, Katherine M. M. Wheelhouse, Simon Woodward, Hon Wai Lam
Summary: Chiral dienes are important ligands in asymmetric catalysis but they are difficult to obtain. In this study, a simple chiral allenecarboxanilide was used to produce pseudoenantiomeric bicyclo[2.2.2]octa-2,5-dienes containing an alkenyl bromide via intramolecular [4+2] cycloaddition. These compounds can be easily functionalized to provide diverse chiral diene ligands. The synthesis is straightforward and can be conducted on a large scale. The resulting ligands exhibit high performance in nine types of enantioselective Rh(I)-catalyzed addition reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.