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1,3-dipolar cycloaddition of Substituted Benzonitrile Oxide to 5-(R)-(l-Menthyloxy)-2(5H)-furanone

Chinese Chemical Letters 2002年第7期13卷 593-596页

作者： HaiHongHUANG QingHuaCHEN 等 InstituteofMateriaMedica ChineseAcademyofMedicalSciences＆PekingUnionMedicalCollegeBeijing100050 DepartmentofChemistry BeijingNormalUniversityBeijing100875

Several isoxazoline compounds were obtained by the 1,3-dipolar cycloaddition of benzonitrile oxide to 5-(R)-(l-menthyloxy)-2(5H)-furanone. The reaction condition was investigated preliminarily, the structures of these compounds have been established via the analysis of NMR data(involved NOEID or HMBC) and the reaction seems occurred regioselectively.

关键词： dipolar cycloaddition benzonitrile oxide configuration 1H-NMR NOE.

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Unusual Cycloadducts from the dipolar cycloaddition of Allenyl Perfluoroalkyl Sulfones to Nitrones

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Chinese Journal of Chemistry 2007年第5期25卷 649-652页

作者：王小进刘金涛 Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

The dipolar cycloaddition reaction of allenyl perfluoroalkyl sulfones （1） to nitrones （2） was described. Unlike nonfluorine-containing allenyl sulfones, 1 reacted readily with 2 in ether at room temperatttre and unusual zwitterionic cycloadducts （3） were obtained in good yields due to the strong electron-withdrawing effect of perfluoroalkyl groups. The structure of 3 was characterized by spectral analyses and X-ray crystallography.

关键词： allenyl perfluoroalkyl sulfone nitrone dipolar cycloaddition zwitterion

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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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Construction of bicyclic imidazoline derivatives via dipolar cycloadditions from conjugate addition-proton transfer

Construction of bicyclic imidazoline derivatives via dipolar...

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有机合成创新—产业化的新动力——中国化学会全国第三届有机合成化学与过程学术讨论会

作者： Zhang,Xiaohui~* Guo,Ming (College of Environment and Chemical Engineering,Dalian University,Dalian 116622)

Azomethine ylides,defined by Huisgen,are planar molecules composed of one nitrogen atom and terminal sp carbons and belong to a class of azomethine obtained which lead to 1,3-dipolar cycloaddition reaction. cycloaddition reactions minimise the number of separate bond-forming steps by generating several bonds simultaneously,and 1,3-dipolar cycloadditions are an obvious way to apply this strategy to heterocycles.

关键词： imidazoline dihydroimidazolium ylide dipolar cycloaddition proton-transfer

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Asymmetric Trapping of Pd-Containing Dipoles by Photogenerated Ketenes

Asymmetric Trapping of Pd-Containing Dipoles by Photogenerat...

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中国化学会·第十六届全国有机合成化学学术研讨会

作者：陆良秋 Yi Wei Miao-Miao Li Jie Liu Wen-Jing Xiao 华中师范大学 College of Chemistry Central China Normal University

Transition metal-catalyzed cycloaddition reactions have been determined to be a powerful tool for constructing valuable heterocyclic *** particular,a variety of dipolar cycloidditions of in situ generated,transition metal-containing dipolar species have been established by reacting with a series prepared *** the past years,we are focused on the development of Pd-,Ir-,Fe-and Cu-catalyzed novel dipolar cycloadditions by exploiting new reactivity,new reagent and new ligand. Recently,we successfully expanded the concept of TM-containing dipoles to the asymmetric photochemical cycloaddition reactions. As depicted in Scheme 1,the key to success is the enantioselective trapping of Pd-containing intermediates by ketenes,a class of reactive C2-synthons,which were generated in an in-situ and traceless manner under visible light *** this trapping,a variety of chiral heterocycles bearing challenging chiral quaternary stereocenters can be accessed in a facile manner with good efficiency and high enantio selectivity.

关键词： asymmetric catalysis palladium catalysis dipolar cycloaddition ketene chiral heterocycle

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