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ynamide Protonation-Initiated Cis-Selective Polyene Cyclization and Reaction Mechanism

CCS Chemistry 2022年第9期4卷 2991-3001页

作者： Jiasheng Yao Chen-Long Li Xing Fan Zhou Wang Zhi-Xiang Yu Junfeng Zhao School of Pharmaceutical Sciences Guangzhou Medical UniversityGuangzhou 511436 College of Chemistry and Chemical Engineering Jiangxi Normal UniversityNanchang 330022 College of Chemistry Peking UniversityBeijing 100871 School of Chemistry and Chemical Engineering Northwestern Polytechnical UniversityXi’an 710072 State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071

The diastereoselectivity of conventional polyene cyclization reactions is highly dependent on the configuration of the internal alkenes,where E-poly enes provide trans-decalins,while Z-polyenes offer cis-decalins.Although polyene cyclization has evolved into a reliable and widely used strategy for the construction of trans-decalin frameworks of terpene and steroid natural products,its application for cis-decalin framework is extremely challenging.

关键词： polyene cyclization cis-decalin framework ynamide protonation double protonation mechanism

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Et2Zn-promoted β-trans-selective hydroboration of ynamide

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Chinese Chemical Letters 2020年第6期31卷 1564-1567页

作者： Kefeng Wang Zixi Zhuang Huihui Ti Peishan Wu Xin Zhao Honggen Wang Key Laboratory of Molecular Target&Clinical Pharmacology State Key Laboratory of Respiratory DiseaseSchool of Pharmaceutical Sciences&The Fifth Affiliated HospitalGuangzhou Medical UniversityGuangzhou 511436China Guangdong Key Laboratory of Chiral Molecule and Drug Discovery School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China Guangdong Institute of Analysis(China National Analytical Center Guangzhou)Guangzhou 510070China

The trans-hydroboration of alkyne represents a challenging task in organic synthesis.Reported herein is an Et2 Zn promotedβ-trans hydroboration of ynamides by using N-heterocyclic carbene(NHC)-ligated borane as boryl source.The reaction leads to a stereoselective construction of enamides bearing a valuable boryl substituent.Both aromatic and aliphatic ynamides were applicable to the reaction.Synthetic transformation of the C-B bond in the product via Suzuki-Miyaura coupling provides a simple and stereospecific route to multi-substituted enamides.Mechanistic studies were conducted and the possible mechanism was discussed.

关键词： Hydroboration ynamide NHC-borane Et2Zn Enamid

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Oxoarylation of ynamides with N-aryl hydroxamic acids

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Chinese Chemical Letters 2021年第8期32卷 2551-2554页

作者： Changwei Chen Hongyu Zhang Gang Xu Sunliang Cui College of Pharmaceutical Sciences Zhejiang UniversityHangzhou 310027China College of Chemical and Biological Engineering Zhejiang UniversityHangzhou 310058China

ynamides are electron-rich alkynes with unique reactivities and act as flexible building blocks in organic synthesis.Therefore,the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting.Herein,we report an oxoarylation of ynamides with N-aryl hydroxamic acids.In the presence of catalytic Cu(OTf)_(2),both the terminal and internal ynamides could undergo an addition/[3,3] sigmatropic rearrangement cascade with N-aryl hydroxamic acids to achieve oxoarylation,along with providing selective entry to(ortho-amino)arylacetamides and oxindoles.Moreover,deuterium-labelling reaction and gram-scale reaction were conducted to probe the mechanism and showcase the scalability.

关键词： ynamide Hydroxamic acid Oxoarylation Oxindole Rearrangement

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One-pot synthesis of tetrahydroindoles via a copper catalyzed N-alkynation/[4+2] cycloaddition cascade

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Chinese Chemical Letters 2019年第1期30卷 266-268页

作者： Chun Jiang Piao-Piao Yu Qing Zhang Hua-Dong Xu Mei-Hua Shen School of Pharmaceutical Engineering & Life Science Changzhou University

A CuSO_4 catalyzed ynamide formation/[4+2] cycloaddition relay reaction was achieved in one-pot.Various 4,7-cis-dihydroindolines were produced in good to high yields. The one-pot operation in conjunction with the chea... 详细信息

关键词： Tetrahydroindole N-Alkynation Intramolecular [4+2]cycloaddition Copper catalysis ynamide Relay reaction

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Awakening Sleeping Beauty:Vinyl Esters for Macrolactonization

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Chinese Journal of Chemistry 2021年第4期39卷 1022-1024页

作者： Qi Song Luyao Kong Lili Zhu Ran Hong Sha-Hua Huang School of Environmental and Chemical Engineering Shanghai Institute of Technology100 Haiquan RoadShanghai201418 China CAS Key Laboratory of Synthetic Chemistry of Natural Substances Center for Excellence in Molecular SynthesisShanghai Institute of Organic Chemistry(CAS)345 Lingling RoadShanghai200032University of Chinese Academy of Sciences19A Yuquan RoadBeijing100049 China

Macrolactones play a critical role in pharmaceuticals and agrochemicals.Numerous efforts have been devoted to developing synthetic methods for them.We highlighted a recent progress for building macrocycles(≥12-member... 详细信息

关键词： Acetylene Amide bond Macrolactonization Vinyl ester ynamide

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ynamide-Mediated Thioamide Substituted Peptide Synthesis

Ynamide-Mediated Thioamide Substituted Peptide Synthesis

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第十一届全国化学生物学学术会议

作者：赵军锋江西师范大学

Thioamide substitution has evolved into an important tool for the chemical biology of peptides and proteins. However,exploration of its full potential has been hampered by insufficient synthetic strategies for site-specific introduction of a thioamide bond to a peptide backbone.We recently disclosed that ynamides could be used as racemization-free coupling reagents for peptide synthesis. Herein,we reported a novel ynamide-mediated two-step thioamide bond formation strategy which could be used for site-selectively incorporating of a thioamide substitution into a peptide backbone. The α-thioacyloxyenamide intermediates formed as the major product of the addition reactions of ynamides and monothiocarboxylic acids are stable and can be purified,characterized and stored.The appropriate balance between their activity and stability enables them to be effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions.Notorious issues such as racemization/epimerization and the use of toxic and smelly thionating reagents,which persecute thiopeptide synthesis for a long time,have been addressed.Importantly,the modular nature of the ynamide-mediated thioamide bond formation makes this strategy amenable to site-specific incorporating of a thioamide bond to peptide backbone not only in solution-phase peptide synthesis but also in solid-phase peptide synthesis.

关键词： ynamide thioacylating reagent solid phase peptide synthesis thioamide

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