Article
Chemistry, Organic
Zhan-Cai Ma, Lin-Wen Wei, Yuan Huang
Summary: We have developed a highly efficient stereodivergent [4 + 2] annulation reaction using palladium catalysis to synthesize N-heterocycles with 1,3-nonadjacent stereogenic centers. The diastereoselectivity of the reaction is dependent on the polarity of solvents used. Additionally, good enantioselectivities were achieved by employing the chiral ligand Wingphos.
Article
Chemistry, Organic
Manisha Sharma, Pankaj Tamanna, Pankaj Chauhan
Summary: An unprecedented stereoselective route has been developed for synthesizing polyfunctionalized hydrophenanthren-2(1H)-ones with multiple stereogenic centers. The use of a bifunctional squaramide enabled a domino reaction sequence, providing direct access to the desired compounds with high enantio- and diastereoselectivity.
Article
Chemistry, Organic
Xiaoyi Li, Zihao Li, Rong Zhang, Zhen Zhou, Yonghui Zhang, Yi Xia, Weijun Yao, Zhen Wang
Summary: An organocatalyzed stereoselective domino reaction for the synthesis of multicyclic spirooxindole derivatives bearing two stereogenic quaternary carbon atoms is reported. The chiral thiourea catalyst with alkyl substitution efficiently tolerates a wide range of substrates, yielding spirooxindole derivatives with an O,O-acetal-fused tricyclic skeleton or tetrahydroxanthone moiety in moderate to good yields and excellent selectivities. The products generated from this method show promising anticancer activities.
Article
Chemistry, Multidisciplinary
Alena Budinska, Helma Wennemers
Summary: This article presents a mild and efficient organocatalytic method for the stereoselective synthesis of chiral triflones using alpha-aryl vinyl triflones, previously unexplored in asymmetric synthesis. The products can be easily derivatized into disubstituted delta-sultones, gamma-lactones, and pyrrolidine heterocycles, highlighting their synthetic versatility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Hanyue Qiu, Zhuanzhuan Du, Yankun Zhao, Shan Yuan, Song Xi, Tao Zhou, Jiao Yang, Changhui Zhang, Yang Xiong, Yi Xia, Shaolin Zhang, Lin Fu, Ling He, Min Zhang
Summary: This study presents a series of multisubstituted pyrrolidines with four continuous stereogenic centers, including up to two quaternary stereogenic centers. Through systematic evaluations, compound 4m was identified as a potent antiproliferation agent with crucial involvement of the quaternary stereogenic centers. This work demonstrates the importance of introducing quaternary stereogenic centers in privileged scaffolds for expanding chemical space and discovering novel therapeutic agents.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiufen Bi, Jia Feng, Xiaoping Xue, Zhenhua Gu
Summary: This report describes a rhodium-catalyzed enantioselective ring-opening/acylation of silafluorenes. The use of a newly developed bulky phosphoramidite ligand and methanol additive allows for the generation of one axial chirality and one silicon-stereogenic center with high selectivity by cleaving only one Si-C bond.
Article
Chemistry, Organic
Bo Yang, Xingfa Tan, Yicong Ge, Yingzi Li, Chuan He
Summary: In this study, an efficient one-pot strategy for the stereodivergent asymmetric synthesis of various P-atropisomeric Si-stereogenic monohydrosilanes with excellent stereoselectivity was developed. This method provides an effective platform for the synthesis of enantioenriched phosphine-based silicon-stereogenic monohydrosilanes, which could have potential applications in asymmetric catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Bo Yang, Xingfa Tan, Yicong Ge, Yingzi Li, Chuan He
Summary: Silicon-stereogenic monohydrosilanes have broad applications, but their combination with phosphines is rare. In this study, an efficient one-pot strategy was developed for the asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes, which have potential applications in asymmetric catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Multidisciplinary Sciences
Feng-Hua Zhang, Xiaochong Guo, Xianrong Zeng, Zhaobin Wang
Summary: The authors described an asymmetric three-component 1,4-dialkylation of 1,3-enynes via dual photoredox and chromium catalysis to provide chiral allenols. This method has a broad substrate scope and good functional group compatibility, while allowing simultaneous control of axial and central chiralities.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Wentan Liu, Jie Ke, Chuan He
Summary: Transition-metal-catalyzed enantioselective C-H functionalization is a powerful tool for synthesizing enantioenriched compounds, with sulfur-based functionalities playing a key role. Recent advances have focused on utilizing sulfur functional groups and chiral sulfoxides to achieve stereoselective C-H functionalization.
Article
Chemistry, Physical
Zhan-Cai Ma, Lin -Wen Wei, Song Liu, Yuan Huang
Summary: The synthesis of spirocyclic frameworks with multiple stereogenic centers through a single transformation is a high-priority challenge in synthetic chemistry. This study reports an unprecedented efficient stereodivergent [4+2] annulation reaction using palladium catalysts to synthesize spiropyrazolones with three contiguous stereogenic centers. Excellent diastereodivergency (up to >20:1) and enantioselectivity (up to >99% ee) have been achieved using different commercially available chiral ligands. This is the first example of employing vinyl benzoxazinanones as the palladium p-allyl precursor for stereodivergent reactions. Density functional theory (DFT) calculations provide insights into the mechanism of this stereodivergent annulation process.
Article
Chemistry, Organic
Sheng Zuo, Yuan Tao, Zhigang Liu, Ke Zhang, Luyun Zhang, Yingtang Ning, Fen-Er Chen
Summary: This study successfully synthesized highly congested indanone-based spirolactones through copper-catalyzed decarboxylative propargylation, with the key role of DPEN-based ligands. The method tolerated a wide range of functional groups, yielding high diastereo- and enantioselectivities. Mechanistic observations indicated the capability of the new copper complex to enable stereocontrolled addition to copper-allenylidene species.
Article
Chemistry, Organic
Elzbieta Lastawiecka, Slawomir Frynas, K. Michal Pietrusiewicz
Summary: Two synthetic protocols have been developed for the conversion of 1-phenylphosphinan-4-ones to novel P-stereogenic 1-phenylphosphin-2-en-4-ones. These transformations provide convenient access to optically active 1-phenylphosphin-2-en-4-one 1-sulfide and 1-oxide with enantiomeric purities of 96% and 55%, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiang Ren, Zhan Lu
Summary: A series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed 1,4-hydroboration of enones with HBpin to access chiral beta,beta-disubstituted ketones with good to excellent selectivities. The protocol is operationally simple and has a broad substrate scope.
Article
Chemistry, Multidisciplinary
Kun Jiang, Shi-Jun Li, Qing-Peng Liu, Ning Yu, Yu-Lin Li, Yu-Qiang Zhou, Kui-Cheng He, Jing Lin, Ting-Yu Zheng, Jian Lang, Yu Lan, Ye Wei
Summary: Bridged tetracyclic nitrogen scaffolds are commonly found in biologically active molecules and medicinally relevant structures. Traditional methods require complex reaction steps and/or specific starting materials. This study presents an unprecedented iminyl radical-triggered relay annulation from oxime-derived peresters and azadienes, which demonstrates good substrate scope, functional group compatibility, and the ability to deliver various bridged aza-tetracyclic compounds with complex molecular topology and four contiguous stereogenic centers in a single operation.
Article
Chemistry, Multidisciplinary
Xiang-Wei Liu, Jiang-Ling Shi, Jiang-Bo Wei, Chao Yang, Jia-Xuan Yan, Kun Peng, Le Dai, Chen-Guang Li, Bi-Qin Wang, Zhang-Jie Shi
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Cayetana Zarate, Ruben Manzano, Ruben Martin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Jia-Xuan Yan, Hu Li, Xiang-Wei Liu, Jiang-Ling Shi, Xin Wang, Zhang-Jie Shi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Xiang-Wei Liu, Yan Yan, Yong-Qiang Wang, Chao Wang, Jian Sun
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Organic
Xiang-Wei Liu, Jiang-Ling Shi, Jia-Xuan Yan, Jiang-Bo Wei, Kun Peng, Le Dai, Chen-Guang Li, Bi-Qin Wang, Zhang-Jie Shi
Article
Chemistry, Multidisciplinary
Li Lin, Zhonglie Yang, Jianchen Liu, Jingxia Wang, Jiale Zheng, Jun-Long Li, Xiaobin Zhang, Xiang-Wei Liu, Hezhong Jiang, Jiahong Li
Summary: An efficient visible-light-induced iodosulfonyl reaction of alkenes in water was accomplished using an EDA complex strategy without the need for transition-metal catalysts and organic solvents. The method showed a broad substrate scope, high chemical selectivity, and was performed at room temperature.
Article
Chemistry, Organic
Xue Tong, Si-Si Luo, Hua Shen, Shu Zhang, Tian Cao, Yi-Peng Luo, Long-Ling Huang, Xi-Tao Ma, Xiang-Wei Liu
Summary: The study reports a method for the direct conversion of C(sp(2))-F bond to C(sp(2))-C(sp(3)) bond using Al(alkyl)(3) as the coupling partner under nickel catalysis. The success of this chemoselective method relies on the fluorophilicity of the aluminum reagent, while showing promising application in late-stage alkylation of fluorinated drug analogues. This method represents an important example of utilizing challenging C-F bonds as alternative electrophiles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xiangwei Liu, Xiabing Li, Baolin Li
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2009)
