Article
Chemistry, Organic
Feng Zhou, Qi-Long Hu, Ke-Qiang Hou, Albert S. C. Chan, Xiao-Feng Xiong
Summary: A convenient strategy for the diastereoselective synthesis of alpha,beta-diamino diacid derivatives bearing congested vicinal acyclic tetrasubstituted stereocenters via catalytic Mannich-type reactions of azlactones and 2-aminoacrylates was established. A diverse set of alpha,beta-diamino diacid derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivity (up to 98:2 er) was achieved by employing the catalyst (DHQD)2PHAL in the subsequent asymmetric study.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jian-Qiang Zhao, Han-Wen Rao, Hui-Ling Qian, Xue-Man Zhang, Shun Zhou, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: A palladium-catalyzed stereoselective decarboxylative allylation method using vinyl methylene cyclic carbonates as allyl precursors was developed, leading to the synthesis of trisubstituted allylic amino acid derivatives. The reaction conditions were mild, and the products exhibited exclusive (Z)-configuration. An alternative protocol utilizing in situ generated azlactones for reacting with vinyl methylene cyclic carbonates was also explored to prepare the same type of amino acid derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Xiao Lin, Boming Shen, Ziyang Wang, Yuyu Cheng, Xuling Chen, Pengfei Li, Peiyuan Yu, Wenjun Li
Summary: In this study, an asymmetric organocatalytic reaction was developed for the first time, enabling the remote 1,10-addition of alkynyl indole imine methides generated in situ from alpha-(6indolyl) propargylic alcohols with thiazolones. The reaction yielded axially chiral tetrasubstituted allenes featuring vicinal sulfur-containing quaternary carbon stereocenters, with high yields and excellent stereoselectivities. The scalability of the reaction and the chemical transformations of the 1,10-adduct were also investigated. Control experiments and DFT calculations were conducted to elucidate the reaction mechanism.
Article
Chemistry, Applied
Laura A. Bryant, Kenneth Shankland, Hannah E. Straker, Callum D. Johnston, Nicholas R. Lees, Alexander J. A. Cobb
Summary: The article describes a rare organocatalytic intramolecular cyclization of resorcinols with a high enantioselectivity using a specific organocatalyst. The obtained bicyclic resorcinols show excellent utility in the synthesis of cannabinoid-like compounds, and exhibit anticonvulsant activity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ziyang Wang, Xiao Lin, Xuling Chen, Pengfei Li, Wenjun Li
Summary: A chiral phosphoric acid-catalyzed enantioselective 1,6-conjugate addition of thiolacetic acid to alkynyl indole imine methide in situ formed from alpha-(3-indolyl) propargylic alcohol has been developed, enabling the formation of axially chiral sulfur-containing tetrasubstituted allenes in generally high efficiency with stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Qiang Zhang, Jingxiang Pang, Tian-Zhang Wang, Feng Chen, Minghao Shen, Tianyu Li, Yongshuai Chai, Yu-Feng Liang, Jie Sun, Zhushuang Bai
Summary: An enantioselective organo-catalyzed reaction of furanones with alpha,ss-unsaturated ketones is developed for the efficient synthesis of chiral bicyclic γ-butyrolactones with high yields, enantioselectivities, and diastereoselectivities. Further transformations of the obtained products are demonstrated. A diamine mediated catalytic cycle is proposed as the reaction mechanism.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Ruslan A. Kovalevsky, Maxim Smirnov, Alexander S. Kucherenko, Kseniya A. Bykova, Elizaveta Shikina, Sergei G. Zlotin
Summary: In this study, 2-nitroallylic carbonates were used for the first time as promising biselectrophilic C3 synthons. They reacted with kojic acid derivatives in a bifunctional squaramide catalyzed asymmetric domino reaction, yielding nitro compounds that contain two hydroxypyranone units. The reaction products undergo noncatalytic epimerization at the carbon atom next to the nitro group. A plausible mechanism of the epimerization based on reversible formation of intermediate aci-nitro compound is proposed. The double addition products were transformed into configurationally stable acetates and chiral nitro glutarates, which are promising precursors for chiral amino glutaric acid derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ramasamy Jayarajan, Tautvydas Kireilis, Lars Eriksson, Kalman J. Szabo
Summary: In this study, a variety of aliphatic, aromatic, and heterocyclic boronic acids were successfully modified using trifluorodiazoethane and BINOL derivatives, resulting in the synthesis of chiral trifluoromethyl containing boronic acid derivatives. The conversion of the chiral boronic acids to other compounds in situ was also demonstrated.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Mariliis Kimm, Ivar Jarving, Maksim Oseka, Tonis Kanger
Summary: Asymmetric rearrangement reactions are highlighted as a perfect tool for constructing new carbon-carbon bonds in an enantioselective manner. The article specifically discusses a new and straightforward procedure for synthesizing alpha-hydroxy ketones with high diastereo- and enantioselectivity through the enantioselective [2,3]-Wittig rearrangement of cinnamyloxycyclohexanone derivatives catalyzed by a commercially available primary amine.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wen-Cheng Li, Lei Yang, Zhong-Lin Wei, Wei-Wei Liao
Summary: A straightforward diastereo- and enantioselective Claisen rearrangement/oxa-Michael addition tandem sequence with a cinchona squaramide catalyst was developed for the synthesis of valuable dihydropyrans. The organo-bifunctional catalyst played a crucial role in enhancing the stereoselectivity in this asymmetric tandem sequence. Additionally, good yields and moderate stereoselectivities were achieved in the asymmetric catalytic sequential processes of hydroalkoxylation/Claisen rearrangement/cyclization and Claisen rearrangement/aza-Michael addition tandem sequences.
Article
Chemistry, Organic
Prasenjit Gayen, Prasanta Ghorai
Summary: A highly chemoselective 1,2-addition of thiols with 2-isothiocyanatochalcones followed by an enantioselective intramolecular thia-Michael addition cascade has been developed for the synthesis of enantioenriched [1,3]-benzothiazine derivatives. The squaramide catalyst derived from cinchona provides excellent yield and enantioselectivity with a wide range of substrates. Furthermore, this strategy can be extended to access enantioenriched organophosphorus-substituted [1,3]-benzothazines using diphenylphosphine oxide nucleophile.
Article
Chemistry, Multidisciplinary
Jinzhao Li, Yuhao Mo, Liqiao Yan, Xiaoming Feng, Zhishan Su, Xiaohua Liu
Summary: This paper describes an organocatalytic asymmetric [8+2] higher-order cycloaddition of tropones with azlactones using bifunctional guanidines as catalysts, resulting in the synthesis of a wide range of [5.3.0] bicyclic compounds with high yields and excellent diastereo- and enantioselectivity. The method also allows for rapid transformation into enantioenriched alpha-amino acid derivatives, demonstrating significant synthetic utility.
Article
Chemistry, Multidisciplinary
Emmanuel Deau, Alexandra Le Foll, Clemence Fouache, Emilie Corrot, Laetitia Bailly, Vincent Levacher, Pierric Marchand, Florian Querniard, Laurent Bischoff, Jean-Francois Briere
Summary: An unprecedented enantioselective conjugate addition reaction of sodium bisulfite to various nitrostyrenes was achieved with the influence of a bifunctional amino-thiourea organocatalyst, leading to a straightforward route to unprotected chiral taurine derivatives by reducing the obtained beta-nitroethanesulfonic acids into the corresponding amino derivatives.
CHEMICAL COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Xingguang Li, Meng Duan, Peiyuan Yu, K. N. Houk, Jianwei Sun
Summary: Catalytic asymmetric dearomatization is a powerful method for constructing diverse chiral cyclic molecules from readily available arenes. The authors demonstrate an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition, showcasing excellent remote chemo-, regio-, and stereocontrol with chiral phosphoric acid catalysis. This protocol can be extended to the asymmetric dearomatization of other heteroarenes and involves hydrogen bonding for selectivity control as demonstrated by control experiments and DFT calculations.
NATURE COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Hong-Hao Zhang, Feng Shi
Summary: Catalytic atroposelective synthesis of axially chiral indole derivatives is of considerable importance and has become an emerging focus of research. By designing indole-derived platform molecules and developing strategies for organocatalytic transformations, we have successfully synthesized structurally diversified indole derivatives with axial chirality. These platform molecules possess versatile and unique reactivity, allowing for the synthesis of various axially chiral indole derivatives.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Zhixuan Zeng, Xudong Xun, Liwu Huang, Jiecheng Xu, Gongming Zhu, Guofeng Li, Wangsheng Sun, Liang Hong, Rui Wang
Article
Chemistry, Organic
Guofeng Li, Guangjun Bao, Gongming Zhu, Yiping Li, Liwu Huang, Wangsheng Sun, Liang Hong, Rui Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Organic
Guofeng Li, Ying Yao, Zheng Wang, Man Zhao, Jiecheng Xu, Liwu Huang, Gongming Zhu, Guangjun Bao, Wangsheng Sun, Liang Hong, Rui Wang
Article
Chemistry, Medicinal
Xiaomin Guo, Jing Rao, Tiantian Yan, Bangzhi Zhang, Wenle Yang, Wangsheng Sun, Junqiu Xie
Summary: The study found that Feleucin-K59 with alpha-(4-Pentenyl)-Ala substitution has enhanced antimicrobial activity, improved stability, and no hemolytic activity or resistance. It also showed potent antibiofilm activity in vitro and better antimicrobial and antibiofilm activities against drug-resistant bacteria in in vivo experiments. The mechanism of action involves disrupting the cell membrane and binding to intracellular DNA, making it difficult for bacteria to develop resistance.
ACS INFECTIOUS DISEASES
(2021)
Article
Biochemistry & Molecular Biology
Xiaomin Guo, Tiantian Yan, Jing Rao, Xin Yue, Xiong Pei, Jiahui Deng, Wangsheng Sun, Wenle Yang, Bangzhi Zhang, Junqiu Xie
Summary: Improvements made to Feleucin-K3 by introducing unnatural amino acids resulted in synthetic peptides with enhanced antimicrobial activity and stability. Among these analogs, N-terminal-substituted analog K65 and C-terminal-substituted analog K70 demonstrated superior antimicrobial activity, especially against multidrug-resistant bacteria, with increased stability in salt and serum environments. These peptides effectively inhibited biofilm formation, showing promising efficacy against MRSA infections, and operated by permeating the outer membrane and depolarizing the cytoplasmic membrane to induce cell death as part of their antimicrobial mechanism.
Article
Chemistry, Organic
Yiping Li, Jingyue Li, Guangjun Bao, Changjun Yu, Yuyang Liu, Zeyuan He, Peng Wang, Wen Ma, Junqiu Xie, Wangsheng Sun, Rui Wang
Summary: In this study, a novel coupling reagent NDTP was explored, which exhibited mild, nonirritating, convenient availability, and recyclability. It could activate carboxylic acids via acyl thiocyanide and enable the rapid synthesis of amides and peptides under mild conditions. Furthermore, the methodology was compatible with Fmoc-SPPS, providing an alternative approach for peptide manufacturing.
Article
Chemistry, Organic
Ming Zhang, Man Zhao, Ying Wang, Lu Chen, Bohan Liu, Xiaobin You, Wangsheng Sun, Liang Hong, Guofeng Li
Summary: This article reports a photo and Cu-mediated radical-radical approach that enables the one-step synthesis of the phthalideisoquinoline skeleton. N-aryl phthalideisoquinolines with various substituents were synthesized in moderate to good yields under mild reaction conditions. The bioactivity data showed that a new compound 4x efficiently inhibits the growth of multiple tumor cell lines, with more than 10-fold enhancement by significantly increasing G2/M arrest compared to noscapine.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ming Zhang, Man Zhao, Ying Wang, Lu Chen, Guofeng Li, Bohan Liu, Xiaobin You, Wangsheng Sun, Liang Hong
Summary: A one-step synthesis of the phthalideisoquinoline skeleton was achieved using a photo and Cu-mediated radical-radical approach. N-aryl phthalideisoquinolines with various substituents were synthesized in moderate to good yields under mild reaction conditions. Bioactivity testing showed that compound 4x exhibited potent inhibition of multiple tumor cell lines by significantly increasing G(2)/M arrest compared with noscapine.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Guangjun Bao, Peng Wang, Xiaomin Guo, Yiping Li, Zeyuan He, Xinyi Song, Ruiyao E, Tingli Yu, Junqiu Xie, Wangsheng Sun
Summary: This study has revealed a visible-light mediated deoxygenative radical addition of carboxylic acids to dehydroalanines. The method has a wide range of applications in the synthesis of beta-acyl alanine derivatives and peptide modification, providing a new tool for the rapid construction of bioactive peptide analogues.
Article
Chemistry, Organic
Junxian Yang, Zeyuan He, Liang Hong, Wangsheng Sun, Rui Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Guofeng Li, Man Zhao, Junqiu Xie, Ying Yao, Lingyun Mou, Xiaowei Zhang, Xiaomin Guo, Wangsheng Sun, Zheng Wang, Jiecheng Xu, Jianzhong Xue, Tao Hu, Ming Zhang, Min Li, Liang Hong
Article
Chemistry, Multidisciplinary
Gongming Zhu, Guangjun Bao, Yiping Li, Wangsheng Sun, Jing Li, Liang Hong, Rui Wang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
