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Dual Palladium/Scandium Catalysis toward Rotationally Hindered C3-Naphthylated Indoles from β-Alkynyl Ketones and o-Alkynyl Anilines

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Chinese Journal of Chemistry 2021年第1期39卷 106-114页

作者： Dan Wang Shi-Chao Wang Wen-Juan Hao shu-jiang tu Bo jiang School of Chemitry&Materials Science Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional MaterialsJiangsu Normal UniversityXuzhouJiangsu 221116Chino

A new dual plldium/scandium catalysis starting fromβ-alkynyl ketones and o alkynyl anilines is reported for the first time,leading to the atom-economic synthesis of rotationally hindered C3-naphthylated indoles in moderate to good yields and high *** method can tolerate normal air conditions,and features the use of palladium/scandium cooperative catalysts without any ligand,facile double annulation involving various internal alkynes,and good functional group tolerance.

关键词： Dual metallic catalysis Regioselectivity Benzannulation Arylated indoles Internal alkynes

Gold Self-Relay Catalysis Enabling[3,3]-Sigmatropic Rearrange-ment/Nazarov Cyclization and Allylic Alkylation Cascade for Constructing All-Carbon Quaternary Stereocenters

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Chinese Journal of Chemistry 2022年第6期40卷 687-692页

作者： Fan-Tao Meng Xiao-Yan Qin Jing Li Tian-shu Zhang shu-jiang tu Bo jiang Wen-Juan Hao School of Chemistry&Materials Science Jiangsu Normal UniversityXuzhouJiangsu 221116China School of Materials and Chemical Engineering Xuzhou University of TechnologyXuzhouJiangsu 221018China

Molecular scaffolds endowed with all-carbon quaternary stereocenter are ubiquitous in natural products and significant bioactive ***,efficient construction of this type of structure units is full of challenge due to their congested chemical ***,we report a new gold(Ⅰ)self-relay catalysis merging[3,3]-sigmatropic rearrangement/Nazarov cyclization with al-lylic alkylation starting from 1,3-enyne acetates and allylic alcohols,producing a wide range of synthetically important allyl cyclo-pentenones with an all-carbon quaternary stereocenter in good yields under mild *** protocol demonstrates the precise control of regioselectivity,high functional group tolerance of substrates and the low loading of gold catalyst without inert atmos-phere protection,providing a catalytic and efficient entry to all-carbon quaternary stereocenters.

关键词： Allylation Domino reactions Carbocycles Gold self-relay catalysis 1,3-Enynes

Gold self-relay catalysis for accessing functionalized cyclopentenones bearing an allcarbon quaternary stereocenter

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Organic Chemistry Frontiers 2022年第1期9卷 140-146页

作者： Fan-Tao Meng Jing-Long Chen Xiao-Yan Qin Tian-shu Zhang shu-jiang tu Bo jiang Wen-Juan Hao School of Chemistry&Materials Science Jiangsu Normal UniversityXuzhou221116P.R.China School of Materials and Chemical Engineering Xuzhou University of TechnologyXuzhou 221018P.R.China

A new gold(I)self-relay catalysis consisting of a 3,3-rearrangement,Nazarov cyclization and Michael addition cascade of 1,3-enyne acetates with aurones and their derived azadienes is reported,and used to produce a series of densely functionalized cyclopentenones bearing a cyclic quaternary stereocenter in moderate to good yields under mild *** tandem protocol demonstrates high regioselectivity,broad substrate flexibility and good functional group tolerance of substrates without inert atmosphere protection,providing a catalytic and convergent approach for creating all-carbon stereoscopic centers.

关键词： catalysis quaternary functional

Michael Addition Reaction without Catalyst: The Synthesis of 2-Amino-5, 6, 7, 8-tetrahydro-5-oxo-4-aryl-7, 7-dimethyl- 4H-benzo-[b]-pyran Derivatives

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Chinese Chemical Letters 2002年第5期13卷 393-395页

作者： shu jiang tu Xiao Hong LIU Heng Jun MA Da Qing SHI Fang LIU Department of Chemistry Xuzhou Normal UniversityXuzhou 221009

A series of tetrahydrobenzo-[b]-pyran derivative was synthesized by the reaction of arylmethylene malononitrile or arylmethylene cyanoacetate with dimedone in ethylene glycol at 80C without catalyst. The structures o... 详细信息

关键词： Benzo-[b]-pyran dimetone ethylene glycol.

Catalytic Enantioselective Construction of 6-4 Ring-Junction All-Carbon Stereocenters and Mechanistic Insights

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Chinese Journal of Chemistry 2022年第15期40卷 1767-1776页

作者： Jia-Yin Wang Chen-Long Li Ting Xu Meng-Fan Li Wen-Juan Hao shu-jiang tu Jianyi Wang Guigen Li Zhi-Xiang Yu Bo jiang School of Chemistry&Materials Science Jiangsu Normal UniversityXuzhouJiangsu 221116China College of Chemistry Peking UniversityBeijing 100871China Medical College Guangxi UniversityNanningGuangxi 530004China Institute of Chemistry&Biomedical Sciences Nanjing UniversityNanjingJiangsu 210093China Department of Chemistry and Biochemistry Texas Tech UniversityLubbockTexas 79409-1061United States

Comprehensive Summary Developing reactions for the synthesis of 6-6-4 and 6-4 carbocyclic scaffolds with a chiral quaternary center at the bridgehead position is highly desired,considering the existence of such skeletons in natural products with biological activities and the potential of using these molecules for downstream studies in chemical biology and medicinal *** here is accessing these target skeletons with high chemo-,regio-and enantio-selectivities through Pd(ll)/chiral N,N'-disulfonyl bisimidazoline(Bim)ligand-catalyzed asymmetric reaction of yne-allenones and arylboronic acids.

关键词： Asymmetric catalysis Palladium Michael addition Chiral cyclobutenes Mechanism

Domino bicyclizations in the construction of several fused heterocyclic skeletons

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Domino bicyclizations in the construction of several fused h...

Bicyclization Reactions toward Functionalized Hetero-and Carbocycles

中国化学会第九届全国有机化学学术会议

作者： Bo jiang shu-jiang tu School of Chemistry and Chemical Engineering Jiangsu Normal University

＜正＞Domino bicyclization reactions have emerged as effective methods for the assembly of complex cyclic structures by the combination of two or more distinct reactions into a one-pot *** reactions can not only enhan...

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Bicyclization Reactions toward Functionalized Hetero-and Car...

Studies on New Transformations of Yne-Allenones

中国化学会第十四届全国有机合成化学学术研讨会

作者： Wen-Juan Hao Bo jiang shu-jiang tu School of Chemistry & Materials Science jiangsu Normal University

Bicyclization reactions have emerged as effective methods for the assembly of complex cyclic structures of chemical and pharmaceutical interest by the combination of two or more distinct reactions into a one-pot transformation, enabling their multiple reactive sites to react each other to construct two new rings in a single step. These reactions feature annulation efficiency, extreme convergence while minimizing the generation of waste. Bicyclization reactions include three types of intramolecular, two-component, and multi-component modes. Our interest focused on the latter two bicyclization cascade using some readily available starting materials, and a series of novel carbo and heterocyclic compounds involving in more complex structures with in part original nucleus were synthesized(Scheme 1). The starting materials have been maximized to convert into the desired compounds, avoiding time-consuming and energy-costing processes that involve multi-step syntheses. Therefore, these reactions offer a valuable addendum to methodology for the synthesis of hetero and carbocycles.

关键词： multi-component reaction bicyclization carbocycles heterocycles

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Studies on New Transformations of Yne-Allenones

Stereoselective construction of azepine-containing bridged scaffolds via organocata-lytic bicyclization of yne-allenone esters with nitrones

中国化学会·第十六届全国有机合成化学学术研讨会

作者： Wen-Juan Hao 姜波 shu-jiang tu School of Chemistry & Materials Science Jiangsu Normal University 江苏师范大学

Yne-allenones are types of competent reactants endowed with multiple reactive sites,which could be used as versatile and synthetically useful feedstocks for the construction of molecules containing multiple ***,catalytic cyclization of yne-allenones offers a flexible and reliable method for the synthesis of biologically interesting cyclic structures in a convergent manner. These reactions feature annulation efficiency,extreme convergence while minimizing the generation of *** interest focused on cyclization cascade using yne-allenones as starting materials,and a series of novel carbo and heterocyclic compounds involving in more complex structures with in part original nucleus were synthesized(Figure 1). The starting materials have been maximized to convert into the desired compounds,avoiding time-consuming and energy-costing processes that involve multi-step ***,these reactions offer a valuable addendum to methodology for the synthesis of hetero-and carbocycles.

关键词： [2+2] Cycloaddition Nucleophilic Addition Domino Synthesis Carbocycles Heterocycles

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Chinese Chemical Letters 2023年第4期34卷 309-312页

作者： Meng-Fan Li Shao-Qing Shi Ting Xu Qian Zhang Wen-Juan Hao shu-Liang Wang Jianyi Wang shu-jiang tu Bo jiang School of Chemistry and Materials Science and jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials Jiangsu Normal UniversityXuzhou 221116China Medical College Guangxi UniversityNanning530004China

A new organocatalytic double annulation cascade involving scission/recombination of N-O bonds of nitrones is reported for the first time, and used to produce a range of hitherto unprecedented tricyclic bridged-fused benzo[d]azepines bearing three stereogenic centers with moderate to good yields and complete diastereoselectivity. A quinine-catalyzed reaction of yne–allenone esters with nitrones worked well and provided a convergent and regioselective pathway to access these three-dimensional scaffolds from the planar conjugated system. Density functional theory(DFT) calculations have been applied to understand the key process for forming diradical intermediates.

关键词： Bicyclization Diastereoselectivity Organocatalysis Bridged heterocycles YNE-allenone esters Nitrones