Article
Chemistry, Multidisciplinary
Minghui Zhu, Qinglong Zhang, Weiwei Zi
Summary: The study presents a dual-metal catalyzed diastereodivergent coupling method for the synthesis of beta-amino alcohols with multiple stereoisomers, enabling the concise preparation of natural products such as mycestericins F and G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Jing-Fei Wu, Nan-Wei Wan, Ying-Na Li, Qing-Ping Wang, Bao-Dong Cui, Wen-Yong Han, Yong-Zheng Chen
Summary: A dual-enzyme cascade strategy was developed for regiodivergent and stereoselective hydroxyazidation of alkenes, leading to the synthesis of various enantiomerically pure 1,2-azidoalcohols. This approach combines the asymmetric epoxidation of alkenes and regio-selective ring opening of epoxides with azide catalyzed by styrene monooxygenase and halohydrin dehalogenase. Additionally, a one-pot chemo-enzymatic route to chiral beta-hydroxytriazoles from alkenes was achieved by combining biocatalytic cascades and Cu-catalyzed azide-alkyne cycloaddition.
Article
Chemistry, Organic
Wei Xie, Liang Zhao, Xinmei Fu, Rong Zhang, Xinyu Hao, Chunying Duan, Yaming Li
Summary: A new strategy for the synthesis of beta-amino alcohols and beta-amino ethers was developed, involving the three-component functionalization of olefins with sulfoxyimidoylsulfonium salt and a nucleophilic reagent using photoredox catalysis. The sulfoxyimidoylsulfonium salt plays a crucial role as the N-centred radical precursor. The strategy allows for the synthesis of beta-amino alcohols and beta-amino ethers with various functional groups in good yields under mild conditions, and offers the advantages of improved safety, no additives, and easy accessibility of raw materials.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Wei Wen, Qi-Xiang Guo
Summary: This article summarizes the recent advances in the application of chiral aldehyde catalysis in asymmetric reactions and prospects its future development.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Tufan K. Mukhopadhyay, Dirk Trauner
Summary: A general strategy to quickly access glycerophospholipids is reported in this study, utilizing the opening of a phosphate triester epoxide with carboxylic acids catalyzed by Jacobsen's Co(salen) complex. This method allows for the synthesis of various glycerophosphate derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yaoyu Liang, Jie Luo, David Milstein
Summary: In this study, a new reaction of acceptorless dehydrogenative coupling of epoxides and amines to form amides catalyzed by ruthenium pincer complexes is reported. This reaction shows high yield and selectivity, and is significant in various academic and industrial fields.
Article
Chemistry, Physical
Ashis Das, Luca Buzzetti, Mikus Purins, Jerome Waser
Summary: In this study, we report an enantioselective palladium-catalyzed reaction, which utilizes a trifluoroacetaldehyde-derived tether to react with propargylic amines, generating chiral oxazolidines. Through diastereoselective hydrogenation using a heterogeneous palladium catalyst, protected benzylic amino alcohols can be obtained with yields of 45-87% and enantiomeric excess (ee) values of 84-94%. A catalytic amount of aryl iodide is required for the hydroalkoxylation of alkynes, highlighting the important role of a putative Pd(II)/ArI oxidative addition complex in promoting the oxypalladation/protodemetalation reaction.
Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Subramanian Thiyagarajan, Chidambaram Gunanathan
Summary: This review provides an overview of catalytic hydrogenation of epoxides to alcohols, including the hydrogenation of both terminal and internal epoxides and the summary of both homogeneous and heterogeneous hydrogenation. The selectivity, efficiency, and reaction mechanisms of these reactions are also highlighted.
CHEMISTRY-AN ASIAN JOURNAL
(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, Applied
Sk Abu Saleh, Atanu Hazra, Saumen Hajra
Summary: The catalyst and organic solvent-free regioselective hydroperoxylation method allows for the synthesis of secondary benzylic beta-hydroperoxy amines and alcohols, as well as tertiary 3-hydroperoxy oxindoles, and is also applicable to less reactive alkyl aziridines. Additionally, an acid-catalyzed Kornblum-DeLaMare type rearrangement of secondary benzylic hydroperoxide has been discovered to produce amino- and hydroxyl ketones.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Faju Li, Linhong Long, Yan-Mei He, Zeyu Li, Hui Chen, Qing-Hua Fan
Summary: A unique family of chiral macrocyclic ligands with a tunable saddle-shaped cavity is described. Using their manganese(I) complexes, the first example of earth-abundant transition metal-catalyzed asymmetric formal anti-Markovnikov hydroamination of allylic alcohols was achieved, providing a practical access to synthetically important chiral gamma-amino alcohols. The study revealed the remarkable role of the macrocyclic framework in the reaction process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Marvin Titze, Juliane Heitkaemper, Thorsten Junge, Johannes Kaestner, Rene Peters
Summary: Enantiopure secondary alcohols are high-value synthetic building blocks, and a new concept for catalytic hydroboration has been proposed with exceptional catalytic turnover numbers. The catalyst, accessible in few steps, is stable, recyclable, and efficient for at least 10 times of reuse.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ziqi Zhu, Jieshuai Xiao, Mingjie Li, Zhuangzhi Shi
Summary: This study reports for the first time that chiral nickel complexes can catalyze the intermolecular enantioselective addition of aryl iodides across aldehydes, providing diverse optically active secondary alcohols. The method has a broad substrate scope and mild reaction conditions, avoiding the traditional pre-generation of organometallic reagents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Jianyu Xu, Olivia P. Bercher, Michael R. Talley, Mary P. Watson
Summary: The development of mild, nickel-catalyzed cross-couplings for the preparation of highly enantioenriched products, including those with quaternary stereocenters, has expanded the synthetic toolbox. This perspective highlights the use of convenient and functional-group-tolerant organoboron reagents, as well as the discoveries of activating groups and conditions that have led to highly stereospecific reactions. Emphasis is placed on mechanistic understanding and controlling inversion vs retention pathways, while also discussing limitations and future development opportunities.
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
Jiawang Liu, Zhaobin Han, Xiaoming Wang, Zheng Wang, Kuiling Ding
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
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)