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One-pot remote desymmetrization/Peterson-olefination for the construction of silicon-stereogenic silyl ethers

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Science China Chemistry 2023年第10期66卷 2797-2802页

作者： Wengang Guo Qian Li Yan Liu Can Li State Key Laboratory of catalysis Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023China

Chiral silyl ethers and silanols are important synthetic intermediates and bioactive *** this work,we developed a onepot remote desymmetrization/Peterson-olefination of silacyclopentene oxides with benzoic acids in the presence of Martin’s *** new methodology not only realizes the atom-economy of Peterson olefination,but also represents a catalytic method for synthesis of silicon-stereogenic silyl *** a bulky chiral phosphoric acid 4i as organocatalyst,the reactions proceeded efficiently to afford various olefin-functionalized organosilyl ethers in excellent diastereoelectivities(up to 25/1 d.r.)and high enantioselectivities(up to 94%ee).

关键词： asymmetric catalysis silicon-stereogenic silyl ether remote desymmetrization/Peterson-olefination bronsted acid catalysis

Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles

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Chinese Chemical Letters 2024年第4期35卷 330-335页

作者： Yaping Zhang Wei Zhou Mingchun Gao Tianqi Liu Bingxin Liu Chang-Hua Ding Bin Xu Department of Chemistry Affiliated Nantong Hospital of Shanghai University(The Sixth People's Hospital of Nantong)Shanghai Engineering Research Center of Organ RepairInnovative Drug Research CenterSchool of MedicineShanghai UniversityShanghai 200444China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

A facile Tf OH-catalyzed oxidative cyclization of allyl compounds and isocyanide has been developed with the assistance of DDQ, where isocyanide is used as the crucial "N" and "CN" sources. Highly functionalized 2-cyanopyrroles are constructed efficiently through a new formal [3 + 2] mode, demonstrating diverse reactivity and synthetic utility in organic chemistry. 2-Cyanopyrrole is converted into a nucleobase analogue of Remdesivir and 5H-pyrrolo[2,1-a]isoindole through a three-step or a two-step sequence, respectively. This protocol features broad substrate scope, operational simplicity and good functional group tolerance.

关键词： Isocyanide Cyanopyrrole Insertion Allyl compound bronsted acid catalysis

Br?nsted acid catalyzed addition of N^1-p-methyl toluenesulfonyl triazole to olefins for the preparation of N^2-alkyl 1,2,3-triazoles with high N^2-selectivity

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Chinese Journal of catalysis 2016年第8期37卷 1222-1226页

作者：石津玮朱莉莉闻建陈自立中国人民大学化学系北京100872 周口师范大学化学与化学工程学院河南周口466001

An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of m... 详细信息

关键词： bronsted acid catalysis N2-alkyl 1,2,3-triazole N1-toluenesulfonyl triazole Olefin reaction High N2-selectivity