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Elaboration of phosphoramidite ligands enabling palladium-catalyzed diastereo-and enantioselective all carbon [4+3]cycloaddition

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Science China Chemistry 2020年第7期63卷 911-916页

作者： Xing Zheng Hao Sun Wu-Lin Yang wei-ping deng Shanghai Key Laboratory of New Drug Design School of PharmacyEast China University of Science and TechnologyShanghai 200237China

A palladium-catalyzed diastereo-and enantioselective all carbon [4+3] cycloaddition of trimethylenemethane was developed by employing the elaborate tetrahydroquinoline-derived phosphoramidite ligand. The exclusive regioselectivity was realized by using the aromatization-driven diene indole-2,3-quinodimethanes, affording biologically important cyclohepta[b]indoles with excellent diastereo-, and enantioselectivities(up to >20:1 dr, >99% ee). Furthermore, the more challenging pyrrolidone-3,4-dienes, in the absence of aromatization force, were also compatible inthereaction, providing novel cyclohepta[c]pyrrol-1(2H)-ones with excellent regio-, diastereo-, and enantioselectivities(up to >20:1 rr, >20:1 dr, >99% ee).

关键词： asymmetric catalysis |4+3|cycloaddition electron-deficient dienes palladium

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Construction of 3-Azabicyclo[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines via Tandem Michael Addition and Copper-Mediated Oxidative Carbanion Cyclization

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Chinese Journal of Chemistry 2021年第3期39卷 666-670页

作者： Hui Xu Teng Han Xiaoyan Luo wei-ping deng Shanghai Key Laboratory of New Drug Design and School of Pharmacy East China University of Science and Technology130 Meilong RoadShanghai 200237China

Main observation and conclusion A facile synthetic method for the construction of 3-azabicyclo[3.1.0]hexane in the presence of copper catalyst system was *** reaction proceeds through Michael addition of allylamines with allenes followed by copper-mediated intramolecular oxidative carbanion 5-exo-trig radical cyclization,affording potential biologically active 3-azabicyclo[3.1.O]hexane derivatives in moderate to high yields(42%-85%).

关键词： Oxidative coupling Allenes Allylamine 3-Azabicyclohexane Miachel addition

Catalytic asymmetric dipolar cycloadditions of indolyl delocalized metal-allyl species for the enantioselective synthesis of cyclopenta[b]indoles and pyrrolo[1,2-α]indoles

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Science China Chemistry 2021年第1期64卷 34-40页

作者： Fei Tian Wu-Lin Yang Tao Ni Jian Zhang wei-ping deng Shanghai Key Laboratory of New Drug Design and School of Pharmacy East China University of Science and TechnologyShanghai 200237China

The development of novel synthons and efficient methods to synthesize chiral polycyclic indoles has been a hot topic in organic synthesis and medicinal chemistry owing to their broad applications in medicines,pesticides,and other functional ***,we disclosed novel indolyl substituted metal-allyl zwitterionic intermediates through the decarboxylation of conveniently available vinyl indoloxazolidones,which could be regarded as two types of dipolar species through the anionic *** palladium-π-allyl species tended to serve as an all-carbon 1,3-dipole in the asymmetric[3+2]cycloaddition with electrondeficient alkenes,which furnished polysubstituted cyclopenta[b]indoles with high regio-and ***,the iridium-π-allyl species was recognized as an aza-1,3-dipole in asymmetric[3+2]cycloaddition with in situ generated C1 ammonium enolates,affording pyrrolo[1,2-α]indoles with high diastereo-and *** addition,the dipolar cycloadditions could be easily scaled-up and several synthetic transformations of the cycloadducts were demonstrated for the rapid synthesis of diverse chiral polycyclic indoles.

关键词： palladium catalysis iridium catalysis asymmetric synthesis dipolar cycloaddition polycyclic indoles

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Synergistic Copper and Chiral Lewis Base Catalysis for the Asymmetric Synthesis of Pyrrolo[1,2-a]indoles

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Chinese Journal of Chemistry 2021年第12期39卷 3292-3296页

作者： Jia-Huan Shen Fei Tian Wu-Lin Yang wei-ping deng Shanghai Key Laboratory of New Drug Design and School of Pharmacy East China University of Science and Technology130 Meilong RoadShanghai 200237China

The first asymmetric decarboxylative[3+2]-cycloaddition of ethynyl indoloxazolidones with carboxylic acids has been developed under synergistic catalysis of copper and chiral Lewis *** protocol provides a direct and modular approach to biologically important pyrrolo[1,2-a]indoles bearing two vicinal stereogenic centers with excellent diastereo-and enantioselectivities(up to>20:1 dr and>99%ee).In addition,the utility of this methodology was demonstrated by scaled-up reaction and several synthetic transformations of the cycloadduct.

关键词： Copper Lewis base Synergistic catalysis Pyrrolo[1,2-a]indoles Asymmetric synthesis

Nickel(II)-Catalyzed Diastereo- and Enantioselective [3+2] Cycloaddition of a-Ketoesters with 2-Nitrovinylindoles and 2-Nitrovinylpyrroles

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Chinese Journal of Chemistry 2019年第3期37卷 216-220页

作者： Wu-Lin Yang Zhong-Tao Sun Hao Sun wei-ping deng Shanghai Key Laboratory of New Drug Design and School of Pharmacy East China University of Science and Technology130 Meilong RoadShanghai 200237China

Summary of main observation and conclusion The catalytic asymmetric [3+2] cycloaddition of a-ketoesters w让h 2-nitrovinylindoles and 2-nitrovinylpyrroles has been established. This strategy allowed the construction of structurally diverse pyrrolo[l,2-a]indoles bearing three contiguous stereocenters in generally high yields and good to excellent stereoselectivities (up to 98% yield,>98:2 dr, 99% ee). The efficient synthesis of tetracyclic psychotropic compound analogue via the derivatization of cycloadduct showed the great synthetic potential of this strategy.

关键词： catalytic asymmetric Enantioselective

Synthesis of Indole-Fused Eight-Membered Oxa-Rings via Palladium-Catalyzed Asymmetric[4+4]Cycloaddition of Indole-2,3-Quinodimethanes with 2-Alkylidenetrimethylene Carbonates

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Chinese Journal of Chemistry 2024年第24期42卷 3393-3398页

作者： Xinhao Lu Yi Wang Chenghan He Yang-Zi Liu wei-ping deng Key Laboratory of the Ministry of Education for Advanced Catalysis Materials College of Chemistry and Materials ScienceZhejiang Normal UniversityJinhuaZhejiang321004 China Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism School of PharmacyEast China University of Science and TechnologyShanghai200237 China School of Science and Engineering The Chinese University of Hong KongShenzhenGuangdong518172 China

Comprehensive Summary We report a palladium-catalyzed asymmetric[4+4]cycloaddition reaction between 2-alkylidenetrimethylene carbonate and electron-deficient indole-2,3-quinodimethanes(IQDMs).This reaction features exclusive regioselectivity,high yield(up to 98%),excellent enantioselectivity(up to 95%ee),and easy scale-up without any loss of efficiency,making it valuable for the synthesis of indole-fused eight-membered oxa-rings.

关键词： Pd-catalyzed Asymmetric[4+4]cycloaddition Indole-2,3-quinodimethanes 2-Alkylidenetrimethylene carbonates Indole-fused eight-membered oxa-rings

Catalytic Enantioselective Formal Synthesis of MDM2 Antagonist RG7388 and Its Analogues

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Chinese Journal of Chemistry 2020年第5期38卷 435-438页

作者： Xue-Jie Zou Wu-Lin Yang Jing-Yan Zhu wei-ping deng Shanghai Key Laboratory of New Drug Design and School of Pharmacy East China University of Science and Technology130 Meilong RoadShanghai 200237China

The catalytic asymmetric 1,3-dipolar[3+2]cycloaddition of azomethine ylides with stilbenes has been established,affording structurally diverse pyrrolidines bearing four contiguous stereocenters with stereo-diversity in generally high yields and good to excellent stereoselectivities(up to 98%yield,99:1 dr,>99%ee).Meanwhile,this strategy allowed the formal synthesis of antitumor drug RG7388(PhaseⅢclinical study)and its analogues in high efficiency.

关键词： stereo Catalytic allowed

Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement

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Science China Chemistry 2023年第10期66卷 2810-2816页

作者： Jian Zhang Jia-Yi Su Yang-Zi Liu Hao Li Quannan Wang wei-ping deng College of Chemistry and Materials Science Zhejiang Normal UniversityJinhua 321004China School of Pharmacy East China University of Science and TechnologyShanghai 200237China

Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement with phosphites has been *** protocol offers a straightforward method for the synthesis of potentially bioactive homoallylic alcohol phosphonates in an efficient and economical *** cascade reaction proceeds under mild conditions with excellent functional group ***,the catalytic asymmetric version has also been explored.

关键词： palladium umpolung allylic alkylation Pudovik addition -phospha-Brook rearrangement

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Palladium-Catalyzed[4+4]Cycloaddition of Homo-TMM All-Carbon 1,4-Dipole Precursors for Construction of Benzofuro[3,2-b]azocines and Furo[3,2-b]azocines

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Chinese Journal of Chemistry 2023年第21期41卷 2825-2831页

作者： Ying Chen Meng Zang weije Wang Yang-zi Liu Xiaoyan Luo wei-ping deng Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism School of PharmacyEast China University of Science and TechnologyShanghai 200237China Key Laboratory of the Ministry of Education for Advanced Catalysis Materials College of Chemistry and Materials ScienceZhejiangNormal UniversityJinhuaZhejiang 321004China

We developed a novel Pd-catalyzed[4+4]cycloaddition of(benzo)furan-derived azadienes with homo-TMM all-carbon 1,4-dipoles in situ generated fromα-allyl malonate derivatives,affording an array of benzofuro[3,2-b]azocines and furo[3,2-b]azocines with good to excellent yields(up to 96%)and exclusive *** methodology featured mild reaction conditions and good functional group *** synthetic utility was demonstrated by a gram-scale ***,the catalytic asymmetric[4+4]cycloaddition version has also been explored.

关键词： Pd-catalyzed [4+4]cycloaddition Homo-TMM 1,4-dipoles Methodology and reactions Medium-ring compounds Regioselectivity