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, Physical
Qiao Ren, Tingting Cao, Chunnian He, Meihua Yang, Haitao Liu, Lei Wang
Summary: The highly atroposelective construction of axially chiral N-arylindolocarbazoles via Rh(II)-catalyzed intermolecular carbene N-H insertion reactions provides a rapid access to enantio-enriched products with moderate to good yields and high enantioselectivities. The synthetic utility of this method is emphasized by late-stage functionalization of representative natural products and bioactive molecules, as well as polyaromatic ring construction and chiral phosphoric acid synthesis from N-arylindolocarbazoles, highlighting its practical value in materials chemistry and catalytic asymmetric synthesis.
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)
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
Lulu Shen, Yin Zheng, Zitong Lin, Tianzhu Qin, Zhongxing Huang, Weiwei Zi
Summary: In this study, a binuclear copper-catalyzed method was developed to generate 2-aminoallyl cations from ethynyl methylene cyclic carbamates, which were then used for the enantioselective (3+2) cycloaddition reaction with indoles to construct chiral pyrroloindolines. This transformation exhibits a novel C1,N-dipolar reactivity for 2-aminoallyl cations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xiaohan Ye, Chenhuan Wang, Shuyao Zhang, Qi Tang, Lukasz Wojtas, Minyong Li, Xiaodong Shi
Summary: This study achieved enantioselective, intermolecular alkene arylamination through gold redox catalysis. Chiral P,N ligands were found to be the optimal choice, enabling alkene aminoarylation with good yields and excellent stereoselectivity. As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage and introduced a new way to conduct gold redox catalysis with stereochemistry control.
CHEMISTRY-A EUROPEAN JOURNAL
(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
Si-Yong Yin, Qiansujia Zhou, Chen-Xu Liu, Qing Gu, Shu-Li You
Summary: The iridium-catalyzed asymmetric C-H alkylation was used for the first time to construct N-N biaryl atropisomers. The method showed good yields (up to 98%) and excellent enantioselectivity (up to 99% ee) for the synthesis of axially chiral molecules based on indole-pyrrole skeleton. This method also allowed the synthesis of N-N bispyrrole atropisomers with high yields and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Peng Zhang, Qi Xu, Xiao-Mei Wang, Jia Feng, Chuan-Jun Lu, Yingzi Li, Ren-Rong Liu
Summary: The first enantioselective synthesis of N-N bisindole atropisomers via palladium-catalyzed construction of one indole skeleton is reported in this study. A wide variety of N-N axially chiral bisindoles were generated with good yields and excellent enantioselectivities through a cascade condensation/N-arylation reaction. The reaction mechanism and enantiocontrol were further investigated using density functional theory (DFT) calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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, Multidisciplinary
Quanxin Peng, Meirong Huang, Guangyang Xu, Yan Zhu, Ying Shao, Shengbiao Tang, Xinhao Zhang, Jiangtao Sun
Summary: An intermolecular enantioselective N-alkylation reaction of 1H-indoles has been developed using a cooperative rhodium and chiral phosphoric acid catalyzed N-H bond insertion reaction. The reaction produces N-alkyl indoles with high yields and excellent enantioselectivities, even with both alpha-aryl and alpha-alkyl diazoacetates. This method requires only a small amount of rhodium catalyst and chiral phosphoric acid, and computational studies provide insights into the mechanism and selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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.