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Double[3+2] cycloaddition of nitrile oxides with allenoates:Synthesis of spirobidihydroisoxazoles

Chinese Chemical Letters 2019年第2期30卷 363-366页

作者： Wei Sun Feng Jiang Honglei Liu Xing Gao Hao Jia Cheng Zhang Hongchao Guo Department of Applied Chemistry China Agricultural University

The double [3 + 2] cycloaddition of allenoates with nitrile oxides is presented. The reaction worked well under mild reaction conditions to give the spirobidihydroisoxazole in moderate to excellent yields with excellent diastereoselectivities. The two dihydroisoxazole rings have been formed via a sequential double [3 + 2] cycloaddition.

关键词： Cycloaddition allenoate Nitrile oxide Spirocyclic heterocyle

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A Novel [3+2] Cycloaddition Reaction of allenoate and Isoquinoline

A Novel [3+2] Cycloaddition Reaction of Allenoate and Isoqui...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Liu,Zhi-Qiang Xue-Shun Jia Department of Chemistry Shanghai University

allenoate has received significant interests in organic synthesis due to its facile preparation and versatile reactivity. For instance,the nucleophilic addition and electrophilic addition reactions with a wide range of substances as well as rearrangements have been well documented.In particular,they were proven to be valuable building blocks in many types of cycloaddition reactions2 In this field,phosphine-catalyzed cycloaddition reaction is of great interest due to simple reagent and structural diversity of the adduct.In 2011,we have reported a [2+2+1] cycloaddition involving allenoate by using isocyanide as nucleophile instead of phosphine. In such case,the allenoate and electron-deficient carbonyl-containing isatin in the presence of isocyanide gave a quick access to spirooxindole.As a continuation of our ongoing research,herein we wish to report that the blending of isoquinoline and allenoate can give a quick access to polycyclic skeletons,which involves an unusual [3+2] cycloaddition.Notably,flexibility of this method allows the rapid synthesis of polycyclic framework with high efficiency.The mechanistic proposal indicates that proton transfer take place to induce the unusual [3+2] cycloaddition in the presence of nitrogen-containing base.This method is also distinguished by its convenient experimental set-up and excellent atom-economy.As a result,the present protocol has potential to be applied in medicinal and synthetic chemistry.

关键词： cycloaddition allenoate isoquinoline

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Isocyanide-Based Multicomponent Reactions and Some Related Cycloaddition Reactions

Isocyanide-Based Multicomponent Reactions and Some Related C...

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中国化学会全国第十一届有机合成化学学术研讨会

作者：李健上海大学理学院化学系

Isocyanide-based multicomponent reactions(IMCRs)have been widely investigated in organic synthesis owing to their inherent features such as atom-and step economy,convergence and diversity. In particular,IMCRs enjoy unique superiority over traditional methods for the rapid and efBcient generation of structurally complex molecules. Recently,we have focused our attention on multicomponent reactions involving isocyanide and allenoate,thus providing a quick access to synthesize five-membered carbocycles and heterocycles. In this process,some interesting cycloaddtion reactions are also observed.

关键词： Isocyanide Multicomponent reaction allenoate Cycloaddition

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Phosphine Catalyzed [3+2] Cycloaddition and Vinylation of Indole-derived α,α-Dicyanoolefins with γ-Substituted allenoates

Phosphine Catalyzed [3+2] Cycloaddition and Vinylation of In...

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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： Chang Yuan Hao Tan Xue-Fei Jiang Si Liu Lu Jiang Qi-Ying Cao Xing-Jie Xu Xiao-Yan Deng Guan-Nan Pan Jian-Yang Chen 崔海磊 Laboratory of Asymmetric Synthesis Chongqing University of Arts and Sciences Key Laboratory of Molecular Target & Clinical Pharmacology Guangzhou Medical University Chongqing Key Laboratory of Environmental Materials and Remediation Technologies Chongqing University of Arts and Sciences 重庆文理学院

We have established a substrate-controlled [3+2] cycloaddition and vinylation of y-allenoates with α,α-dicyanoolefins in the presence of phosphine.Indole-incorporated highly functionalized cyclopentenes can be synthesized in good yields（up to 97% yield）.N-functionalization of indole-derived α,α-dicyanoolefins could also be realized by using nitrogen free indole-derived α,α-dicyanoolefin in the presence of phosphine.In sharp contrast to cyclopentenes obtained in previous studies of phosphine catalyzed [3+2] cycloaddition of y-allenoates with α,α-dicyanoolefin,carbon-carbon double bond shifts in cyclopentene obtained in this study by using γ-aromatic allenoates.

关键词： phosphine cycloaddition allenoate α,α-dicyanoolefin vinylation

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