Article
Chemistry, Multidisciplinary
Zhonglin Liu, Lucas J. Oxtoby, Mingyu Liu, Zi-Qi Li, Van T. Tran, Yang Gao, Keary M. Engle
Summary: The study reports a new method facilitated by a transient directing group for the vicinal fluorofunctionalization of alkenes, leading to the construction of vicinal stereocenters with excellent selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Kaili Zhang, Qixing Liu, Renke He, Danyi Chen, Zhangshuang Deng, Nianyu Huang, Haifeng Zhou
Summary: The asymmetric reduction of C = O bonds of 2-arylidene cycloalkanones using a chiral ruthenium complex as a catalyst and HCOOH/Et3N as a hydrogen source resulted in high yields and high enantiomeric excess. This method is not only suitable for small-scale synthesis, but also applicable for the gram-scale synthesis of pharmaceutically important compounds.
Article
Chemistry, Multidisciplinary
Jie Wang, Xiaotian Qi, Xiao-Long Min, Wenbin Yi, Peng Liu, Ying He
Summary: This study presents a novel approach for the synthesis of axially chiral styrenes through tandem iridium catalysis. The method allows for efficient and selective preparation of chiral ligands needed for asymmetric synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Ming Yu Jin, Qianqian Zhen, Dengmengfei Xiao, Guanyu Tao, Xiangyou Xing, Peiyuan Yu, Chen Xu
Summary: Non-covalent pi interactions play a central role in differentiating enantiomeric substrates in a Sharpless asymmetric dihydroxylation (SAD)-based kinetic resolution.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Yu Mu, Tao Zhang, Yaping Cheng, Wenzhen Fu, Zuting Wei, Wanjun Chen, Guodu Liu
Summary: This study presents an efficient nickel-catalyzed intramolecular reductive cyclization for the synthesis of chiral tetrahydrofurans, demonstrating high stereoselectivity and enantioselectivity with a broad substrate scope. The ligand effects and reaction mechanism were investigated in detail. In addition, the developed method enables the efficient synthesis of complex molecules and potentially opens up new research fields in organic synthesis and chemical biology.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Sushovan Paladhi, Si Joon Park, In-Soo Hwang, Jin Hyun Park, Han Yong Bae, Amol P. Jadhav, Choong Eui Song
Summary: In this study, a biomimetic catalytic retro-aldol reaction using a chiral oligoEG cation-binding catalyst as a mimic of type-II aldolase was described. The investigation of various aldol substrates showed that our biomimetic retro-aldol protocol allows for rapid access to highly enantiomerically enriched aldols with a selectivity factor (s) of up to 70. Additionally, the feasibility of the synthetic strategy for accessing diverse and valuable axially chiral aldehydes was demonstrated.
Article
Chemistry, Organic
Jia-Le Zheng, Fei Liu, Xue Song, Zhi Zhao, Wei Du, Ying-Chun Chen
Summary: In this study, we found that dienones generated from the Morita-Baylis-Hillman carbonates of 2-cyclopentenone under Pd(0) catalysis could be umpolunged through pi-Lewis base activation to form regioselective eta 2-Pd(0) complexes, which then underwent asymmetric inverse-electron-demand oxa-Diels-Alder reaction with alpha-cyano chalcones. This study successfully constructed a range of fused pyran frameworks with dense substitutions and demonstrated excellent stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tao Zhang, Wen-Ao Li, Hong-Cheng Shen, Shu-Sen Chen, Zhi-Yong Han
Summary: An asymmetric Heck-Matsuda reaction targeting acyclic internal alkenes was successfully developed through the strategy of chiral anion phase transfer, resulting in high levels of enantioselectivity in the formation of chiral ketones. The use of a catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for suppressing palladium-hydride-mediated side reactions.
Article
Chemistry, Organic
Bin-Qing He, Xuesong Wu
Summary: A practical method for deoxygenative deuteration of aliphatic alcohols using D2O as the deuterium source is reported. The transformation is promoted by visible light and intermediacy of xanthate anions, leading to the formation of deuterioalkanes with high D-incorporation. The catalysis is carried out by in situ formed deuterated 2-mercaptopyridine, serving as a deuterium atom transfer catalyst and an electron shuttle.
Article
Chemistry, Multidisciplinary
Fabian Severin, Giovanni M. Fusi, Christina Wartmann, Jorg-Martin Neudoerfl, Albrecht Berkessel
Summary: In this study, we report a highly syn-selective epoxidation method for terminal allylic alcohols using a titanium salalen complex catalyst at room temperature and aqueous hydrogen peroxide as oxidant. The results demonstrate that enantiopure terminal allylic alcohols can be efficiently converted to epoxy alcohols with high yields and excellent syn-diastereoselectivity. This method shows great synthetic potential and is demonstrated by the gram-scale preparation of a tetrahydrofuran building block with three stereocenters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Pei Fan, Yujia Mao, Chuan Wang
Summary: Herein, we report a palladium/TBADT-cocatalyzed dehydrogenative cross-coupling reaction that enables the synthesis of various 1,4-diketones from simple allylic alcohols and aldehydes as precursors under mild reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jie Zhang, Yaning Wang, Chang You, Mingying Shi, Xueling Mi, Sanzhong Luo
Summary: We report a synergetic chiral primary amine and rhodium catalysis for the asymmetric coupling of beta-ketocarbonyls and alkynes. This method enables the synthesis of linear allylation products with all-carbon quaternary centers in high regio- and enantioselectivities.
Review
Chemistry, Multidisciplinary
Yingtao Wu, Chao Pi, Yangjie Wu, Xiuling Cui
Summary: Directing group migration has emerged as a practical strategy for transition-metal-catalysed direct C-H activation, leading to highly atom-economical processes and enabling the reusage of directing groups. Progress has been made in developing multitasking directing groups, with the focus on different types of migratable directing groups and their mechanisms, as well as synthetic applications.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Yeongyu Hwang, Seung Beom Baek, Dongwook Kim, Sukbok Chang
Summary: This study presents a tandem iridium catalysis that enables the redox-relay amidation of alkenyl alcohols, offering a new route to various alpha-amino ketones with excellent regioselectivity. Mechanistic investigations reveal that the reaction proceeds via a tandem process involving chain walking and intermolecular nitrenoid transfer, with the assistance of hydrogen bonding.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Chun-Tai Hung, Chun-Wei Lu, Shi-Han Huang, Yin-Feng Lu, Hsiang-Chi Chou, Cheng-Che Tsai
Summary: This research utilizes chiral sulfinamides as nucleophiles in intramolecular allylic substitution and sequential aerobic oxidation with aza-Michael addition reactions, achieving good yields of chiral isoindolines and high diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ming-Guang Rong, Tian-Zhu Qin, Weiwei Zi
Article
Chemistry, Multidisciplinary
Qinglong Zhang, Huimin Yu, Lulu Shen, Tianhua Tang, Dongfang Dong, Weiwei Chai, Weiwei Zi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Qinglong Zhang, Dongfang Dong, Weiwei Zi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Austin C. Durham, Yidong Wang, Yi-Ming Wang
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
Chemistry, Multidisciplinary
Yin Zheng, Tianzhu Qin, Weiwei Zi
Summary: This study presents a method for enantioselective (3 + 2) cycloaddition reactions between palladium-oxyallyl species and electron-deficient nitroalkenes. The transformation, enabled by a hydrogen-bond-donating ligand (FeUrPhos) and an inverse electron demand pathway, allows for the assembly of cyclopentanones with up to three contiguous stereocenters with high enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Weiwei Chai, Qingyang Zhou, Wenna Ai, Yin Zheng, Tianzhu Qin, Xiufang Xu, Weiwei Zi
Summary: This study presents a novel method for the (3+2) cycloaddition reactions of palladium-oxyallyl species with 1,3-dienes, leading to the formation of five-membered carbocycles with C-C bond formation. The research also achieved regiodivergent access to cyclopentanones and cycloheptanones by tuning the steric properties of the palladium ligand. The reaction mechanism was investigated using DFT calculation, providing insights into the regioselectivities of the cycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Hong-Fa Wang, Lin-Na Guo, Zhi-Bo Fan, Tian-Hua Tang, Weiwei Zi
Summary: A new dual gold-catalyzed cascade reaction was reported, where the gold catalyst played a role in different steps, facilitating the transformation of alkynes.
Article
Chemistry, Inorganic & Nuclear
Jin Zhu, Austin C. Durham, Yidong Wang, James C. Corcoran, Xiao-Dong Zuo, Steven J. Geib, Yi-Ming Wang
Summary: This study investigated the [3 + 2] cycloaddition reaction of allenyliron complexes as well as the mechanism of isomerization to propargyliron tautomer, presenting evidence for both radical and two-electron mechanisms.
Article
Chemistry, Multidisciplinary
Hongfa Wang, Ruiyuan Zhang, Qinglong Zhang, Weiwei Zi
Summary: A new method for metal-hydride-catalyzed hydroalkylation of 1,3-dienes with aldehydes is described, providing access to chiral molecules with allylic stereocenters. By choosing a combination of chiral palladium and amine catalysts, highly diastereo- and enantioselective access to complementary diastereomers is achieved. The mechanism involves PdH formation and migratory insertion into the alkene, followed by C-C bond formation, with the origin of stereoselectivities investigated through distortion/interaction analysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yidong Wang, Sarah G. Scrivener, Xiao-Dong Zuo, Ruihan Wang, Philip N. Palermo, Ethan Murphy, Austin C. Durham, Yi-Ming Wang
Summary: The study presented a novel iron-catalyzed C-H functionalization reaction, utilizing a specific complex and reagents to achieve the synthesis of a range of novel sulfonamido allene derivatives.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Jin Zhu, Yidong Wang, Aaron D. Charlack, Yi-Ming Wang
Summary: An iridium-catalyzed stereoselective coupling reaction has been developed for the synthesis of 3,4-substituted 1,5-enynes. The reaction shows excellent regio-, diastereo- and enantioselectivities under optimized conditions, and is tolerant to various functional groups. Mechanistic studies revealed the unprecedented dual role of the iridium catalyst, enabling propargylic deprotonation of the alkyne through pi-coordination and generation of a pi-allyl species from the allylic ether starting material.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Ruihan Wang, Yidong Wang, Ruiqi Ding, Parker B. Staub, Christopher Z. Zhao, Peng Liu, Yi-Ming Wang
Summary: A newly-developed cationic cyclopentadienyliron dicarbonyl complex enables the conversion of propylene to its allylic C-C bond coupling products under catalytic conditions. This approach is also applicable to the allylic functionalization of simple alpha-olefins with distinctive branched selectivity. Experimental and computational studies reveal the allylic deprotonation of the metal-coordinated alkene as the turnover-limiting step and provide insights into the multifaceted roles of the newly designed ligand in promoting allylic C-H functionalization with enhanced reactivity and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yue Xia, Nicholas W. Wade, Philip N. Palermo, Yidong Wang, Yi-Ming Wang
Summary: This study presents a novel method using iron catalysis to convert simple monosubstituted allenes into 1-tetrahydroisoquinolinyl 1,1-disubstituted allenes, marking a significant advance in chemical synthesis. The optimized protocol shows a wide scope and mild, functional group tolerant conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yidong Wang, Jin Zhu, Rui Guo, Haley Lindberg, Yi-Ming Wang
