Article
Chemistry, Organic
Kun Wang, Saisai Niu, Xin Guo, Weijun Tang, Dong Xue, Jianliang Xiao, Huaming Sun, Chao Wang
Summary: This research discovers a new method to convert prochiral racemic allylic alcohols to enantioenriched chiral alcohols bearing adjacent stereocenters using a diamine diphosphine Ru complex and tBuOK catalyst. The protocol exhibits a wide substrate scope and high selectivities, and can be applied to the synthesis of enantioenriched chromane and indane compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Helene Pellissier
Summary: Organocatalytic dynamic kinetic resolution (DKR) has emerged as a promising field in the past two decades, allowing efficient separation of chiral compounds. This review aims to provide an update on organocatalytic DKRs since 2016.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaosa Lu, Jie Zhu, Yinhua Huang
Summary: A rhodium-catalyzed highly enantio- and diaster-eoselective alkenylation reaction of Ay-unsaturated butenolides is reported. The use of a chiral diene ligand enables the synthesis of chiral butyrolactones in high yields with extremely high enantioselectivities and high diastereoselectivities. The key process involves the isomerization of butenolides and subsequent dynamic kinetic resolution.
Article
Chemistry, Organic
Baixue Liu, Peng Liu, Xue Wang, Feng Feng, Zhen Wang, Wenqiang Yang
Summary: A general method for the gram-scale enantioselective synthesis of P-stereogenic cyclic phosphine oxides has been developed using copper-catalyzed dynamic kinetic resolution, leading to high yields and high enantioselectivities. The resulting products can be easily reduced to obtain useful P(III)-stereogenic cyclic phosphines. A proposed mechanism involves the unusual rapid racemization of SPOs.
Article
Chemistry, Multidisciplinary
Jia-Hong Wu, Siqiang Fang, Xingtao Zheng, Jiajia He, Yi Ma, Zhishan Su, Tianli Wang
Summary: Efficient and practical methodology has been developed for building two types of phosphorus-installing helicenes via the phosphonium salt catalyzed phospha-Michael reaction together with copper salt enabled aromatization. The scalability and practicality of this protocol were validated by the gram-scale synthesis and transformation of products, particularly towards producing novel helical phosphine ligands that were successfully utilized in metal-catalyzed reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Bin He, Jingyuan Song, Congcong Yin, Gen-Qiang Chen, Xumu Zhang
Summary: Asymmetric hydrogenation of aryldibenzylamino ketones catalyzed by the Ir/f-phamidol system was achieved through dynamic kinetic resolution, producing chiral compounds with high selectivity. This method offers excellent conversion and enantioselectivity, making it applicable in the synthesis of drug candidates and chiral ligands.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Daniel Moock, Tobias Wagener, Tianjiao Hu, Timothy Gallagher, Frank Glorius
Summary: This study presents a method for enantio- and diastereoselective hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis, allowing controlled installation of up to six new defined stereocenters to produce complex octahydrobenzofurans prevalent in bioactive molecules. The unique combination of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor enables the process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Can Li, Rongrong Yu, Song-Zhou Cai, Xianjie Fang
Summary: We have developed a highly diastereoselective method for the synthesis of cyano-substituted cyclopropanes using palladium-catalyzed direct cyanoesterification of cyclopropenes. This method offers mild reaction conditions, good functional group compatibility, and simple operation. The transformation described in this study provides a stepwise, highly atom economic, and scalable approach for obtaining synthetically useful cyclopropanecarbonitriles.
Article
Chemistry, Organic
Ryan R. G. Barrett, Donald A. Campbell, James L. Gleason
Summary: Ethyl diazepane carboxylate catalyzes the oxy-Cope rearrangement of 4-hydroxy- and 4-alkoxy-1,5-hexadiene-2carboxaldehydes via iminium ion activation, leading to cyclopentane-containing products through intramolecular Michael reaction. The reaction is applicable to various substrates, including cyclic and acyclic ones, and shows tolerance towards vinyl substituent substitution. Substrates with cycloalkane framework undergo net ring expansion/cyclopentannulation with high stereocontrol through chairlike transition states. This reaction expands iminium organocatalysis to the oxy-Cope rearrangement within a complexity-generating cascade transformation.
Article
Multidisciplinary Sciences
Fengyuan Guo, Siqiang Fang, Jiajia He, Zhishan Su, Tianli Wang
Summary: This article discusses an organocatalytic asymmetric nucleophilic aromatic substitution reaction, offering a pathway to axial styrene scaffolds via a dynamic kinetic resolution process using a hemiacetal intermediate.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Song Sun, Zhaobin Wang, Shijia Li, Cong Zhou, Lijuan Song, Hai Huang, Jianwei Sun
Summary: This study presents the first organocatalytic kinetic resolution of unactivated aziridines using sulfur nucleophiles, achieving excellent enantioselectivity. A chiral phosphoric acid was identified as an efficient catalyst for intermolecular ring opening under mild conditions, providing highly enantioenriched beta-amino thioethers and aziridines as useful synthetic building blocks.
Article
Chemistry, Organic
Titouan Desrues, Xueyang Liu, Jean-Marc Pons, Valerie Monnier, Jean-Arthur Amalian, Laurence Charles, Adrien Quintard, Cyril Bressy
Summary: This study introduces a new method for the enantioselective synthesis of tertiary alcohols through a chiral isothiourea catalyzed selective acylation of adjacent secondary alcohols, allowing for the preparation of highly enantioenriched monoesters and starting diols. The approach enables the kinetic resolution of racemic diastereoenriched secondary/tertiary diols with s-values exceeding 200.
Article
Chemistry, Organic
Xue-Jiao Lv, Yong-Chao Ming, Hui-Chun Wu, Yan-Kai Liu
Summary: In this study, a Bronsted acid-catalyzed cascade acyclic N,O-hemiaminal formation/oxa-Michael reaction was developed for the synthesis of cis-2,6-disubstituted tetrahydropyrans bearing an exo amide group, namely cyclic N,O-aminals. Various different amides were applicable for the reaction sequence using TsOH, and enantioenriched cyclic N,O-aminal scaffolds were obtained by using chiral phosphoric acid. Mechanistic investigations revealed that the good enantioselectivity was attributed to a H2O controlled dynamic kinetic resolution of the in situ formed acyclic N,O-hemiaminal intermediate. Additionally, divergent transformations of the products resulted in various synthetically useful heterocyclic architectures.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Matthew R. Straub, Vladimir B. Birman
Summary: In summary, easily accessible racemic N-Boc-isoxazolidine-5-ones can undergo enantioselective alcoholysis promoted by double hydrogen bond donor amine organocatalysts, leading to their effective kinetic resolution.
Article
Chemistry, Applied
Marta Meazza, Ramon Rios
Summary: This study describes the first synthesis of 2-alkenylquinolines from 2-allylquinolines and alpha,beta-unsaturated aldehydes. The reaction exhibits high regioselectivity and enantioselectivity, with a broad tolerance of functionalities in both the enal aromatic ring and the quinoline.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Pengfei Yuan, Jiean Chen, Jing Zhao, Yong Huang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Fengjin Wu, Leifeng Wang, Jiean Chen, David A. Nicewicz, Yong Huang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Linrui Zhang, Pengfei Yuan, Jiean Chen, Yong Huang
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Qian Wang, Jiean Chen, Yong Huang
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Zhen Wang, Zhiqi He, Linrui Zhang, Yong Huang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Multidisciplinary
Zhiqi He, Feifei Song, Huan Sun, Yong Huang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Review
Chemistry, Multidisciplinary
Hailei Su, Feng Zhou, Ziru Huang, Xiaohua Ma, Kathiresan Natarajan, Minchuan Zhang, Yong Huang, Haibin Su
Summary: This article summarizes and analyzes recent studies on the molecular mechanisms of promising antiviral drugs for COVID-19, focusing on viral targets such as spike glycoprotein and host proteases, aiming to inspire new ideas for drug design and optimization in the future.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Li Li, Baoli Chen, Jiean Chen, Yong Huang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Physical
Fangfang Guo, Jiean Chen, Yong Huang
Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Article
Chemistry, Physical
Zhen Li, Meirong Huang, Xinhao Zhang, Jiean Chen, Yong Huang
Summary: This study reports an organocatalytic four-component relay radical coupling to access a broad spectrum of beta-tertiary-gamma-quaternary carboxylic acid derivatives, overcoming the synthetic bottleneck of introducing sterically demanding side chains. The high site control achieved using a triazolium N-heterocyclic carbene catalyst and a transient acyl trapping strategy allows for the preparation of diversified carboxylic acid derivatives in a single pot.
Article
Chemistry, Applied
Baoli Chen, Li Li, Jiean Chen, Yong Huang
Summary: An organocatalytic protocol has been developed for the direct coupling of aliphatic aldehydes with sulfonium ylides, resulting in the formation of alpha,beta-unsaturated carbonyl compounds with a formyl substituent. The reaction demonstrates mild conditions, convergence, and control of olefin geometry.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Yuxing Cai, Jiean Chen, Yong Huang
Summary: This report describes a successful organocatalytic 1,4-alkylacylation of 1,3-enynes using a ketyl radical generated from single-electron oxidation of the Breslow intermediate as a coupling partner of allenyl radicals. The transformation exhibited remarkable tolerance to both aromatic and radical precursors.
Article
Biochemistry & Molecular Biology
Kalok Chan, Long Thanh Ta, Yong Huang, Haibin Su, Zhenyang Lin
Summary: In this study, a simple molecular representation method was developed using machine learning and artificial intelligence techniques to predict rate constants of aryl bromides in palladium-catalyzed Sonogashira coupling reactions. The results demonstrate the importance of incorporating domain knowledge into machine learning for improved data analysis.
Article
Chemistry, Multidisciplinary
En Li, Qian Wang, Yuxing Cai, Jiean Chen, Yong Huang
Summary: This study highlights the enantioselective phospha-Michael addition reaction leading to alpha-chiral phosphine sulfide, with an essential role of an independent hydrogen-bonding co-catalyst for high enantioselectivity. Divergent derivatizations under mild conditions for generic phosphine and phosphine oxide compounds further emphasize the bridging role of phosphine sulfide.
CELL REPORTS PHYSICAL SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Xinhang Jiang, En Li, Jiean Chen, Yong Huang
Summary: The geometric configuration of olefin products is often controlled by thermodynamics in synthesis, with few methods enabling switching of cis/trans selectivity. However, photosensitized approaches have recently emerged as a powerful tool for accomplishing this task. By utilizing a photo-induced energy transfer process, selective access of chiral allylic fluorides with a cis-olefin geometry is achieved through in situ isomerization of an N-heterocyclic carbene (NHC)-bound intermediate. Preliminary mechanistic experiments suggest the involvement of an energy transfer process in this transformation.
CHEMICAL COMMUNICATIONS
(2021)
