Article
Chemistry, Applied
Yasuaki Fukazawa, Vladimir Yu. Vaganov, Julia V. Burykina, Artem N. Fakhrutdinov, Ruslan I. Safiullin, Felix Plasser, Aleksandr E. Rubtsov, Valentine P. Ananikov, Andrei V. Malkov
Summary: The mechanism of metal-catalyzed asymmetric alkylation of indoles remains uncertain. In this study, the authors investigate the mechanism from both molecular and nano-level perspectives, revealing the role of water and catalyst precursor on reaction selectivity and performance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shu-Sen Li, Shuo Sun, Jianbo Wang
Summary: The catalytic asymmetric trifluoromethylation of cyclic ketones via a Sc-III/chiral bisoxazoline-catalyzed homologation reaction using 2,2,2-trifluorodiazoethane (CF3CHN2) as the CF3 source is an efficient method to generate chiral alpha-trifluoromethyl cyclic ketones with excellent diastereoselectivity and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Melania Gomez-Martinez, Maria del Carmen Perez-Aguilar, Dariusz G. Piekarski, Constantin G. Daniliuc, Olga Garcia Mancheno
Summary: An enantioselective anion-binding organocatalytic approach using versatile N,N-dialkylhydrazones as polarity-reversed nucleophiles is presented. A highly ordered hydrogen-bond network was envisioned between a CF3-substituted triazole-based multidentate HB-donor catalyst, the ionic substrate, and the hydrazone in a supramolecular chiral ion-pair complex. Experimental and computational studies supported the formation of this network, showing the crucial role of the anion as a template unit. The asymmetric reaction provided highly enantiomerically enriched hydrazones that could be further derivatized to value-added compounds with up to three stereocenters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, Physical
Jian-Hua Liu, Qing Zhou, Yao Lin, Zhu-Lian Wu, Tian Cai, Wei Wen, Yan-Min Huang, Qi-Xiang Guo
Summary: In this study, a highly efficient atom-economic asymmetric alpha-allylation method using chiral-aldehyde/palladium catalyst was reported. This method enables the asymmetric alpha-allylation of different 1,3-dienes and allenes with N-unprotected amino acid esters, leading to the synthesis of alpha,alpha-disubstituted chiral alpha-amino acid esters with high efficiency, good yields, and stereoselectivities. No N-allylation byproducts were observed in these reactions. Two reaction models were proposed based on mechanistic control experiments. Overall, this work demonstrates a new approach for preparing structurally diverse chiral amino acids and provides insights for developing chiral-aldehyde catalytic systems.
Article
Chemistry, Multidisciplinary
Wang Yao, Chuan-Jun Lu, Li-Wen Zhan, Yi Wu, Jia Feng, Ren-Rong Liu
Summary: In this study, a palladium-catalyzed enantioselective C-H activation method for pyrroles was reported, which successfully synthesized structurally diverse indole-pyrrole atropisomers with a chiral N-N axis, showing high yields and enantioselectivities. Furthermore, the kinetic resolution of trisubstituted N-N heterobiaryls with more sterically demanding substituents was also achieved. This versatile method enables the rapid and selective functionalization of pyrroles, facilitating the synthesis of valuable and complex N-N atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Hsien-Liang Cho, Chien-Chen Lai, Yi-Hung Liu, Hsiu-Fu Hsu, Shie-Ming Peng, Sheng-Hsien Chiu
Summary: This paper reports the insertion of Pd(II) into an initially achiral rotaxane, resulting in two chiral metallorotaxanes. Chiral additives and chiral TRISPHAT counteranions were used to confirm the existence of chirality and resolve the enantiomers of the C-2-symmetrical N-heterocyclic carbene complex.
Article
Chemistry, Multidisciplinary
Oliver D. Jackson, Ksenia S. Stankevich, Matthew J. Cook
Summary: An auto-tandem catalytic, branched-selective rearrangement of substituted N-alloc-N-allyl ynamides was developed, which provides an easy access to complex quaternary nitrile products with vinylogous stereocentres in excellent diastereoselectivity, including contiguous all-carbon quaternary centres. The stereochemical outcome is determined via a Pd(0) catalysed dipolar ketenimine aza-Claisen rearrangement, and computational studies illustrate the significant role of ligand geometry.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Tao Qin, Guowei Lv, Qi Meng, Ge Zhang, Tao Xiong, Qian Zhang
Summary: An efficient and general radical hydroamination of alkenes has been achieved using Co(salen) as catalyst, NFSI and its analogues as both nitrogen source and oxidant. Mechanistic experiments indicate that the reaction proceeds through a metal-hydride-mediated hydrogen atom transfer and a catalyst-controlled S(N)2-like pathway. Additionally, an unprecedented asymmetric version with good to excellent enantiocontrol was accomplished using a modified chiral cobalt(II)-salen catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Sundaravel Vivek Kumar, Patrick J. Guiry
Summary: We have developed a facile synthetic route for a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands with central and planar chirality. These ligands showed excellent activities and selectivities in asymmetric reactions, leading to enantioenriched pyrrolidines with high yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Margarita Escudero-Casao, Giulia Licini, Manuel Orlandi
Summary: The paragraph discusses the development of transition-metal-catalyzed alpha-arylation of carbonyl compounds, including enantioselective variants. It also mentions a new chiral Cu-bis(phosphine) dioxides catalytic system for selective alpha-arylation of ketones. Preliminary insight into the unusual pairing of bis(phosphine) dioxides with transition-metal catalysts in the reaction mechanism is also provided.
Article
Chemistry, Multidisciplinary
Hui Yang, Zi-Qi Yang, Su-Zhen Zhang, Wen-Wen Zhang, Qing Gu, Shu-Li You
Summary: Chiral dihydrobenzofuran is a valuable synthetic fragment in both medicinal and organic chemistry. Efficient rhodium(III)-catalyzed chemoselective and enantioselective C-H functionalization/[3+2] annulation of N-phenoxyacetamides with 1,3-dienes is reported. In the presence of 5 mol% CpRh complex, various chiral dihydrobenzofurans were synthesized in up to 79% yield and 98% ee. This reaction proceeds under mild conditions with excellent functional group compatibility.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Physical
Chunming Gui, Yuanyuan Peng, Yang Zhou, Yixuan Zheng, Haifeng Wang, Qiongjiao Yan, Hui Zhou, Wei Wang, Fen-Er Chen
Summary: This paper reports the copper-catalyzed asymmetric propargylic substitution reaction, which efficiently synthesizes multifunctionalized products bearing a terminal alkyne unit with good stereoselectivity. The products can also be easily derivatized into other potentially valuable organic compounds, showing great potential for pharmaceutical development.
Article
Chemistry, Multidisciplinary
Esteban Matador, Javier Iglesias-Siguenza, David Monge, Pedro Merino, Rosario Fernandez, Jose M. Lassaletta
Summary: A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines has been developed using N-tert-butylhydrazones as key neutral reagents, leading to the formation of appealing dihydroisoquinoline derivatives with excellent stereocontrol. Experimental and computational data support the generation of highly ordered complexes that play a crucial role in the selective and high-yielding transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Editorial Material
Chemistry, Multidisciplinary
Jinquana Yu, Kuiling Ding
ACTA CHIMICA SINICA
(2015)
Article
Chemistry, Multidisciplinary
Lei Zhang, Zhaobin Han, Xiaoyu Zhao, Zheng Wang, Kuiling Ding
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Yang Li, Zheng Wang, Kuiling Ding
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Article
Chemistry, Multidisciplinary
Hailong Liu, Zhiwei Huang, Zhaobin Han, Kuiling Ding, Haichao Liu, Chungu Xia, Jing Chen
Article
Chemistry, Multidisciplinary
Xubin Wang, Xiaoming Wang, Zhaobin Han, Zheng Wang, Kuiling Ding
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Xinyi Ren, Zhiyao Zheng, Lei Zhang, Zheng Wang, Chungu Xia, Kuiling Ding
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Review
Chemistry, Organic
Linli Zhang, Zhaobin Han, Lei Zhang, Mingxing Li, Kuiling Ding
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Inorganic & Nuclear
Xiaofei Jia, Mengru Zhang, Maohua Li, Fan Pan, Kuiling Ding, Li Jia, Laura A. Crandall, James T. Engle, Christopher J. Ziegler
Article
Chemistry, Multidisciplinary
Jiawang Liu, Ming Nie, Qinghai Zhou, Shen Gao, Wenhao Jiang, Lung Wa Chung, Wenjun Tang, Kuiling Ding
Article
Chemistry, Organic
Xubin Wang, Xiaoming Wang, Zhaobin Han, Zheng Wang, Kuiling Ding
ORGANIC CHEMISTRY FRONTIERS
(2017)
Review
Chemistry, Multidisciplinary
Kaiwu Dong, Rauf Razzaq, Yuya Hu, Kuiling Ding
TOPICS IN CURRENT CHEMISTRY
(2017)
Article
Chemistry, Medicinal
Pengfei Zhou, Yuru Liang, Hao Zhang, Hao Jiang, Kechang Feng, Pan Xu, Jie Wang, Xiaoming Wang, Kuiling Ding, Cheng Luo, Mingming Liu, Yang Wang
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Haixia Wang, Lulu Yu, Mingsheng Xie, Jiang Wu, Guirong Qu, Kuiling Ding, Haiming Guo
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Jiawang Liu, Zhaobin Han, Xiaoming Wang, Fanye Meng, Zheng Wang, Kuiling Ding
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Kuiling Ding
PROGRESS IN CHEMISTRY
(2017)
