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SO_(2)-Insertion induced enantioselective oxysulfonylation to access β-chiral sulfones with quaternary carbon stereocenters

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Science China Chemistry 2024年第3期67卷 908-913页

作者： Jun Zhang Xuefeng Wang Peiqi Wang Jiayuan Fang Shaoyu Li Jie Wu school of pharmaceutical and Chemical engineering&institute for advanced studies Taizhou UniversityShanghai 200438China Department of Chemistry Fudan UniversityShanghai 200438China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China school of Chemistry and Chemical engineering Henan Normal UniversityXinxiang 453007China

β-Chiral sulfones are structural motifs widely found in natural products and bioactive molecules, while also serving as important intermediates for the synthesis of valuable chiral scaffolds. In contrast to the rapid growth of sulfur dioxide insertion chemistry over the last decade, enantioselective catalytic variants for accessing β-chiral sulfones, especially those bearing a quaternary carbon stereocenter, remain rare. Herein, we report an enantioselective copper/bisoxazoline catalyzed oxysulfonylation of alkenes to yield isoxazolinyl-containing β-chiral sulfones bearing quaternary carbon stereocenters with moderate to excellent yields and up to 96:4 er. The advantage and irreplaceability of this sulfur dioxide insertion catalytic system have been demonstrated by achieving transformations clearly unavailable with the previously reported sulfonyl chloride system. Additionally,the recoverability of the new-developed bisoxazoline ligand L9 and its reusability without any erosion of the catalytic activity and enantioselectivity further demonstrate the usefulness of the protocol.

关键词： β-chiral sulfones sulfur dioxide insertion oxysulfonylation copper catalysis enantioselectivity

Narasaka reaction:Desilylative acylation of 1-alkenylsilanes with acid anhydrides

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Chinese Chemical Letters 2021年第9期32卷 2751-2755页

Recent advances in the desilylative acylation of 1-alkenylsilanes with acid anhydrides under transition metal catalysis are *** catalytic desilylative acylation of 1-alkenylsilanes provides an efficient route toα,β-unsaturated ketones by using rhodium or iridium as the ***,various one pot sequence reactions have been developed,which can synthesizeα,β-unsaturated ketones from simple starting materials in an economic ***,this approach is applied to the asymmetric synthesis of atropisomers possessing silanol groups with excellent enantioselectivity.

关键词： Acid anhydride 1-Alkenylsilane Desilylative acylation Transition metal catalysis α,β-Unsaturated ketone

Branched module-modified SN38 prodrug nanoassemblies for improved colorectal cancer therapy:Effectively balance efficacy and safety

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Nano Research 2025年第1期18卷 572-585页

作者： Qing Wang Shiyi Zuo Shufang Zheng Cuiyun Liu Yaqiao Li Jiayu Guo Danping Wang Shuo Wang Wenjing Wang Bowen Zhang Minglong Huang Xianbao Shi Jin Sun Zhonggui He Bingjun Sun Department of Pharmaceutics Wuya College of InnovationShenyang Pharmaceutical UniversityShenyang 110016China Joint International Research Laboratory of Intelligent Drug Delivery Systems Ministry of EducationShenyang Pharmaceutical UniversityShenyang 110016China school of Chemical engineering The University of AdelaideAdelaideSA 5005Australia Department of Pharmacy The First Affiliated Hospital of Jinzhou Medical UniversityJinzhou 121001China

The clinical utility of irinotecan is restricted by individual variability in carboxylesterase *** administration of its active metabolite,7-ethyl-10-hydroxycamptothecin(SN38),presents an appealing alternative due to its potent anti-tumor ***,the undesirable properties of SN38,such as poor water solubility and nontarget toxicity,present significant hurdles to its clinical *** nanoassemblies based on modular design strategy show promise in overcoming these challenges by enhancing drug delivery and selective *** modular design,the modification module plays a crucial role in improving the self-assembly capability of *** current studies mainly focus on using straight aliphatic chains for prodrug design,branched aliphatic chains emerge as superior alternatives warranting further *** this study,we selected 2-heptylundecanol(BAlc18)as modification module to construct an SN38 *** exquisite design,SN38-SS-BAlc18 NPs integrated prominent properties in selfassembly capability,specific activation and biocompatibility,resolving the challenges of irinotecan and SN38,ultimately demonstrating excellent anti-tumor *** exploration enriched the design theory of prodrug nanoassemblies that can effectively balance safety and colorectal anti-tumor efficacy.

关键词： irinotecan SN38 prodrug nanoassemblies disulfide bonds branched aliphatic chains

Recent advances in the applications of[1.1.1]propellane in organic synthesis

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Chinese Chemical Letters 2020年第12期31卷 3065-3072页

作者： Fu-Sheng He Shimin Xie Yanfang Yao Jie Wu school of pharmaceutical and Materials engineering&institute for advanced studies Taizhou UniversityTaizhou 318000China College of Chemistry Xiangtan UniversityXiangtan 411105China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

As a highly strained small molecule,[1.1.1]propellane has been widely used in various synthetic transformations owing to the exceptional reactivity of the central bond between the two bridgehead *** strain-release approaches,the rapid development of strategies for the construction of bicyclo[1.1.1]pentane(BCP)and cyclobutane derivatives using[1.1.1]propellane as the starting material has been witnessed in the past few *** this review,we highlight the most recent advances in this ***,the reactivity of[1.1.1]p ropellane can be divided into three pathways,including radical,anionic and transition metal-catalyzed pathways under appropriate conditions.

关键词： [1.1.1]Propellane Bicyclo[1.1.1]pentane Cyclobutane Radical Transition metal catalysis Photocatalyst

An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO·(SO_(2))_(2) and trimethylsilyl azide

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Organic Chemistry Frontiers 2022年第4期9卷 917-922页

作者： Jun Zhang Junwei Wu Xiaotong Chang Peiqi Wang Jiemin Xia Jie Wu school of pharmaceutical and Materials engineering&institute for advanced studies Taizhou UniversityJiaojiang 318000ZhejiangChina State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling RoadShanghai 200032China school of Chemistry and Chemical engineering Henan Normal UniversityXinxiang 453007China

An iron-catalyzed four-component reaction of cycloketone oxime esters,alkenes,DABCO·(SO_(2))_(2) and tri-methylsilyl azide(TMSN_(3))is *** multicomponent radical transformation presents excellent regio-and chemoselectivity,leading to a range of β-azidosulfones in moderate to excellent *** this protocol,the utilization of a sulfur dioxide surrogate of DABCO·(SO_(2))_(2) as the source of the sulfonyl group enables the reaction to proceed efficiently under mild conditions without the need for strong ***,the products can be transformed intoβ-aminosulfones and other valuable sulfonyl-contain-ing nitrogen heterocycles.

关键词： azide ketone esters

An unexpected iron(Ⅱ)-promoted reaction of N-arylprop-2-yn-1-imines with water:Facile assembly of multi-substituted pyrroles

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Chinese Chemical Letters 2021年第1期32卷 37-39页

作者： Kaida Zhou Jiapian Huang Jie Wu Guanyinsheng Qiu school of pharmaceutical and Materials engineering&institute for advanced studies Taizhou UniversityTaizhou 318000China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China College of Biological Chemical Science and EngineeringJiaxing UniversityJiaxing 314001China

Generation of multi-substituted pyrroles is accomplished through an unexpected iron(Ⅱ)-promoted reaction of N-arylprop-2-yn-1-imines with wate *** transformation proceeds smoothly with excellent chemoselectivityand regioselectivity.A stoichiometric amount of Fe(OTf)_(2) is necessary for the succes s ful conversion.A Lewis acid-promoted tandem reaction pathway is proposed.

关键词： Tandem reaction Iron(Ⅱ)triflate Prop-2-yn-1-imine Pyrrole Water

A photocatalytic radical relay reaction of 2-methylthiolated phenylalkynones and potassium metabisulfite

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Organic Chemistry Frontiers 2022年第2期9卷 450-455页

作者： Yuyan Liu Xinyi Zhang Jiajing Lv Chao Zhang Xiaotong Chang Shengqing Ye Jie Wu school of pharmaceutical and Materials engineering&institute for advanced studies Taizhou University1139 Shifu AvenueZhejiang 318000China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling RoadShanghai 200032China school of Chemistry and Chemical engineering Henan Normal UniversityXinxiang 453007China

The generation of methylsufonyl-containing thioflavones through a radical relay reaction of methylthiolated phenylalkynones and potassium metabisulfite in the presence of a catalytic amount of sodium methylsulfinate as an initiator under photoinduced conditions is *** photocatalytic reaction proceeds smoothly with good functional group tolerance under visible light *** mechanistic investigations indicate that this reaction occurs through a radical relay pathway.

关键词： radical potassium smoothly

Zwitterionic hyaluronic acid derivatives for co-delivery of both chemotherapeutic and nucleic acid drugs in breast cancer treatment

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Nano Research 2025年第1期18卷 607-617页

作者： Ruo-Lin Jiang Hui-Na Liu Yu-Fan Yang Zhi-Cheng Zhang Qi Dai Xiao-Yan Bao Lin-Jie Wu Ya-Xin Qin Xin Tan Xiao-Yan Sun Xu-Fang Ying Zhi-Qing Ben Min Han institute of Pharmaceutics College of Pharmaceutical SciencesZhejiang UniversityHangzhou 310058China Department of Radiation Oncology Key Laboratory of Cancer Prevention and InterventionThe Second Affiliated HospitalCollege of MedicineZhejiang UniversityHangzhou 310058China Hangzhou institute of Innovative Medicine Zhejiang UniversityHangzhou 310058China Jinhua institute of Zhejiang University Jinhua 321299China National Key Laboratory of advanced Drug Delivery and Release Systems Zhejiang UniversityHangzhou 310058China Polytechnic institute Zhejiang UniversityHangzhou 310015China

Traditionally,hyaluronic acid has been widely used for drug delivery,but the current application bottleneck is that hyaluronic acid is hydrophilic and electronegative,which makes it difficult to carry hydrophobic drugs and small interfering RNA(siRNA)with the same *** on previous studies,we designed and synthesized hyaluronic acid nanocarriers HA-spermine/N,N,N-trimethylcystamine/DOX-TPP(HSTD)for loading siRNA to overcome the problem of siRNA release caused by strong electrostatic ***,N,N,Ntrimethylcystamine in the carrier can be degraded by intracellular glutathione to completely and rapidly release siRNA,thus promoting ***,when codelivered with the chemotherapy drug doxorubicin(DOX),this novel nanocarrier showed promising synergy in inhibiting tumor growth.

关键词： zwitterionic hyaluronic acid N N N-trimethylcystamine small interfering RNA(siRNA) doxorubicin

Photoredox-Catalyzed Functionalization of Alkenes w ith Thiourea Dioxide:Construction of Alkyl Sulfones or Sulfonamides

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Chinese Journal of Chemistry 2020年第4期38卷 361-366页

作者： Yuewen Li Jin-Biao Liu Fu-Sheng He Jie Wu school of pharmaceutical and Materials engineering&institute for advanced studies Taizhou University1139 Shifu AvenueTaizhouZhejiang 318000Chino school of Metallurgical and Chemical engineering Jiangxi University of Science and TechnologyGonzhouJiangxi 341000China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Ling ling RoadShanghai 200032China

Summary of main observation and conclusion Sulfonylation of alkenes through photoredox-catalyzed functionalization of alkenes with thiourea dioxide under visible-ight rradiation is achleved,The reaction of alkenes,thiourea dioxide and electropiles provides a green and fficient access to alkyl sul-fones and sulfonamides.A broad reaction scope is presented with good functional group compat bility and excellent regiaselectivity.A plausible mecha-nism involving a radical addition process with sulfur dioxide rpdical anion(SO2-)derived from the oxidation of sulfur dioxide anion(S02^-2) is proposed,which is supported by fluorescence quenching experiments.

关键词： dioxide redox anion