Article
Chemistry, Applied
Liang Xu, Jia Cui, Shan Gao, Jianjun Wang, Jiao Liu, Hongge Jia, Zhuanfang Zhang, Fengjuan Miao, Yu Zang
Summary: Chiral conjugated microporous polymers (CCMPs) containing amide groups were designed and synthesized for the first time as heterogeneous asymmetric catalyst platforms for the stabilization of Pd in asymmetric catalytic synthesis. Four Pd/CCMPs heterogeneous catalysts exhibited efficient catalytic activity and excellent enantioselectivity in the asymmetric Henry reaction, with a wide range of substrates and easy recovery. The Pd/CCMPs composites could be easily recycled and maintained catalytic activity after 3 cycles of reactions.
MICROPOROUS AND MESOPOROUS MATERIALS
(2022)
Article
Chemistry, Physical
Yingqi Xia, Yingtang Ning, Minjie Liu, Fen -Er Chen
Summary: A poly(ethylene glycol) supported amino alcohol has been developed as a chiral ligand for the copper-catalyzed asymmetric nitrolaldol reaction. The catalyst enables the synthesis of syn-2-nitro-1,3-diols with high yields and stereoselectivities. The PEG moiety allows for easy purification and recycling of the catalyst.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Linqing Wang, Haiyong Zhu, Tianyu Peng, Yingfan Xu, Yanzhe Hou, Shixin Li, Shiming Pang, Hailong Zhang, Dongxu Yang
Summary: A catalytic asymmetric hydroxylative dearomatization reaction has been reported, and the resulting products can be easily converted into spiroannulation adducts by treatment with a base under mild conditions. Novel in-situ generated magnesium catalytic methods have been developed using combinational ligands. Related concise transformations of the spiroannulation adducts have been demonstrated.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Sarah R. Moor, James R. Howard, Brenden T. Herrera, Matthew S. McVeigh, Federico Marini, Adrian T. Keatinge-Clay, Eric V. Anslyn
Summary: Characterization of chiral molecules in solution is essential for measuring reaction success. Distinguishing between chiral molecules with multiple stereocenters using optical techniques is challenging. This study presents a technique using circular dichroism spectra and multivariate regression models to predict the speciation of 3-hydroxy-2-methylbutanoic acid stereoisomers, allowing for rapid and accurate determination of enantiomeric excess and diastereomeric excess without chiral chromatography.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Katsuhiko Moriyama, Yukari Oka
Summary: This article reports an enantioselective cascade Michael/hemiaminal formation of alpha,beta-unsaturated iminoindoles with aldehydes using a chiral aminomethylpyrrolidine catalyst bearing a strongly electron withdrawing arylsulfonyl group. The reaction yields anti-2-hydroxy-hydro-1H-pyrido[2,3-b]indole (anti-alpha-carbolinol) derivatives in high yields with high stereoselectivity. DFT calculation studies reveal the importance of multiple hydrogen-bonding interactions in the reaction, and the reaction product can undergo various transformations.
Article
Chemistry, Organic
Manda Sathish, Fabiane M. Nachtigall, Leonardo S. Santos
Summary: In this study, an efficient enantioselective imine reduction method was developed using in situ generated Fethiosquaramides catalysts (Fe-TSQs) 3a and 3b, resulting in the synthesis of chiral tetrahydro-beta-carbolines.
Article
Chemistry, Multidisciplinary
Jialin Qi, Fang Wei, Shuai Huang, Chen-Ho Tung, Zhenghu Xu
Summary: A new method has been developed for the synthesis of sulfur-containing chiral beta-lactams with two consecutive stereogenic centers using copper(I)-catalyzed asymmetric, three-component interrupted Kinugasa reaction. The key lies in the interception of in situ formed chiral four membered copper(I) enolate intermediate with sulfur electrophiles, resulting in good yields and excellent diastereo- and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Swati D. Jadhav, Rupesh C. Patil, Ashutosh A. Jagdale, Suresh S. Patil
Summary: This study presents a sustainable, green, and efficient process for synthesizing 2-nitro alcohol derivatives from different substituted aromatic aldehydes and nitroalkane at ambient temperature with high product yield by using CES as a catalyst. The mild reaction conditions and simple workup are expected to advance environmentally friendly synthesis methods for the Henry reaction. CES, an ecologically safe and inexpensive heterogeneous base catalyst derived from renewable resources, offers a new perspective for this process.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Multidisciplinary
Youcan Zhang, Hui-Qing Geng, Xiao-Feng Wu
Summary: The study presents a palladium-catalyzed four-component perfluoroalkylation/aminocarbonylation reaction, successfully synthesizing various β-perfluoroalkyl amides. The reaction system shows good compatibility with a wide range of substrates, including anilines, alkylamines, and demonstrates good functional-group tolerance and excellent chemoselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Masahiro Kawada, Ryo Tsuyusaki, Kosuke Nakashima, Misaki Yamada, Akihiro Kozakai, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura
Summary: This study presents the first successful example of asymmetric 1,2-additions of nitromethane to trifluoromethyl enones, and achieved highly functionalized products with high yields and excellent enantioselectivities through a novel N,N-dibenzyl diaminomethylenemalononitrile organocatalyst.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Jie Li, Haowen Ma, Xianqiang Zhong, Shanyue Li, Jiehao Zhang, Yunlin Ao, Wei Zhou, Qian Cai
Summary: Spiro beta-lactams are important scaffolds in many bioactive compounds and natural products. The development of new synthetic methods for the formation of structurally diversified chiral spiro beta-lactams is highly important for the discovery of novel bioactive structures. In this work, a copper(I)-catalyzed asymmetric Kinugasa/aldol-type cascade reaction of ketone-tethered propiolamides and nitrones is developed and a set of novel chiral spiro beta-lactams with three contiguous stereogenic centers was achieved in satisfactory yields with high diastereo- and enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Xinxin Lin, Peng Peng, Jianing Guo, Lianhua Xie, Yujia Liu, Zhonghua Xiang
Summary: The study developed a novel steric tetra-imidazole structure to anchor iron in a cross way, enabling the one-step synthesis of atomically dispersed FeN4 rich carbon-based electrocatalysts without the need for pretreatment and acid leaching. This new structure effectively controls the distance between metal rivet centers and inhibits iron aggregation, resulting in high atomic iron loading content and efficient electrocatalytic performance for the oxygen reduction reaction.
Article
Chemistry, Applied
Marcia R. R. Renio, Francisco J. P. M. Sousa, Nelia C. T. Tavares, Artur J. M. Valente, M. Elisa da Silva Serra, Dina Murtinho
Summary: The enantioselective Henry reaction is an important carbon-carbon bond forming reaction that requires the use of efficient chiral catalysts. In this study, in situ formed complexes of N-substituted dihydroxypyrrolidines were evaluated as catalysts, showing that the nature of the N-substituent significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, with products having er up to 92:8 (R:S).
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jialin Qi, Fang Wei, Chen-Ho Tung, Zhenghu Xu
Summary: An innovative asymmetric multicomponent, interrupted Kinugasa allylic alkylation (IKAA) reaction has been developed, providing a high-yield and high stereoselective synthesis of alpha-quaternary chiral beta-lactams that cannot be produced with existing methods. A key feature of this reaction is the stereoselective coupling of transient organometallic intermediates formed in situ with two catalytic amounts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chao Yao, Yaoqi Chen, Chao Wang, Ruize Sun, Haotian Chang, Ruiheng Jiang, Lin Li, Xin Wang, Yue-Ming Li
Summary: Chiral O-N-N tridentate ligands designed from proline and BINOL were evaluated for their performance in a copper(II)-catalyzed asymmetric Henry reaction. The study found that the stereoselectivity of the reaction could be controlled by adjusting the structure and substituents of the ligand.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
