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Organic Chemistry Frontiers 2022年第1期9卷 32-38页

作者： Jitan Zhang Manyi Wu Hu Ju Haitao Yang Baiyang Qian Ke Ding Jiaping Wu Meihua Xie Key Laboratory of Functional Molecular Solids(Ministry of Education) Anhui Key Laboratory of Molecular Based MaterialsCollege of Chemistry and Materials ScienceAnhui Normal UniversityWuhu 241002China.

A silver-catalyzed,K_(2)S_(2)O_(8)-mediated protocol to access regioselective acylarylation of unactivated alkenes was developed.The reaction between N-allyl-indoles andα-oxocarboxylic acids proceeded smoothly and involved an acyl radical addition/C–H cyclization cascade.The protocol showed a broad substrate scope and good tolerance of functional groups.The reaction proceeded with both internal and terminal alkenes to furnish many functional pyrrolo[1,2-a]indoles bearing the ketone carbonyl group,and this feature also provides the potential to construct structurally complex N-containing heterocycles.

关键词： silver allyl radical

Acid-mediated decarboxylative C–H coupling between arenes and O-allyl carbamates

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Organic Chemistry Frontiers 2022年第6期9卷 1711-1718页

作者： Camilla Loro Julie Oble Francesca Foschi Marta Papis Egle MBeccalli Sabrina Giofrè Giovanni Poli Gianluigi Broggini Dipartimento di Scienza e Alta Tecnologia Universitàdegli Studi dell’Insubriavia Valleggio 922100 ComoItaly Sorbonne Université Facultédes Sciences et IngénierieCNRSInstitut Parisien de Chimie MoléculaireIPCM4 place Jussieu75005 ParisFrance DISFARM Sezione di Chimica Generale e Organica“A.Marchesini”Universitàdegli Studi di Milanovia Venezian 2120133 MilanoItaly

Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)_(2) or TMSOTf as promoters affords N-substituted 1-arylpropan-2-amines,1,2-diarylpropanes,1,1-diarylpropanes,or indanes,depending on the nature of the promoter and of the aryl substrates.A full mechanistic rational allowing appreciation of the outcome of these novel C–H based cascades is proposed.An initial acid promoted decarboxylative/deamidative Friedel–Crafts allylation takes place.After protonation of the allylated arene,evolution of the resulting cation may follow different paths depending on the nature of the arene partner and of the allyl moiety in the carbamate.

关键词： allyl moiety coupling

Construction of axially chiral styrene-type allylamines via chiral phosphoric acid-catalyzed asymmetric reductive amination

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Organic Chemistry Frontiers 2022年第3期9卷 764-770页

作者： You-Dong Shao Jin-Shuo Feng Dan-Dan Han Kang-Hui Pan Ling Zhang Yi-Fan Wang Zhong-Hui Ma Pei-Ru Wang Mingjing Yin Dao-Juan Cheng School of Chemistry and Chemical Engineering Heze UniversityHeze 274015China School of Pharmacy Anhui University of Chinese MedicineHefei 230012China

The first enantioselective synthesis of axially chiral styrene-type allylamines was achieved through chiral phosphoric acid mediated atroposelective reductive amination of 1-enal substituted 2-naphthols.This protocol features a broad substrate scope,good enantioselectivities(up to 90%ee)and mild reaction conditions,thus providing a new entry to the challenging atropisomeric acyclic styrene scaffolds.

关键词： styrene chiral allyl

A combined experimental and computational study of NHC-catalyzed allylation of allenoate with MBH esters:new regiospecific and stereoselective access to 1,5-enyne

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Organic Chemistry Frontiers 2022年第1期9卷 51-57页

作者： Fang Sun Fangfang Lu Xue Song Wenchao Wu Kai Zhang Chenxia Yu Tuanjie Li Donghui Wei Changsheng Yao Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials School of Chemistry and Materials ScienceJiangsu Normal UniversityXuzhouJiangsu 221116P R China. The College of Chemistry and Molecular Engineering Zhengzhou University100 Science AvenueZhengzhouHenan 450001P R China

An NHC-catalyzed regiospecific allylation ofα-substituted allenoates with MBH carbonates derived from aryl aldehyde furnished highly functionalized 1,5-enynes bearing a quaternary carbon successfully.Combining with DFT calculations,the reaction mechanism of this conversion was proposed.This method has the advantages of high regioselectivity,good yields and mild reaction conditions.This transformation not only provided a new access to 1,5-enyne,but also enriched the chemistry of allenoates and NHC catalysis.

关键词： conditions catalysis allyl

allyl isothiocyanate ameliorates lipid accumulation and inflammation in nonalcoholic fatty liver disease via the Sirt1/AMPK and NF-κB signaling pathways

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World Journal of Gastroenterology 2019年第34期25卷 5120-5133页

作者： Chun-Xiao Li Jian-Guo Gao Xing-Yong Wan Yi Chen Cheng-Fu Xu Ze-Min Feng Hang Zeng Yi-Ming Lin Han Ma Ping Xu Chao-Hui Yu You-Ming Li Department of Gastroenterology the First Affiliated HospitalCollege of MedicineZhejiang UniversityHangzhou 310003Zhejiang ProvinceChina Clinical Research Center for Hepatobiliary and Pancreatic Diseases of Zhejiang Province Hangzhou 310003Zhejiang ProvinceChina

BACKGROUND allyl isothiocyanate(AITC),a classic anti-inflammatory and antitumorigenic agent,was recently identified as a potential treatment for obesity and insulin resistance.However,little is known about its direct impact on the liver.AIM To investigate the effect and underlying mechanism of AITC in nonalcoholic fatty liver disease(commonly referred to as NAFLD).METHODS To establish a mouse and cellular model of NAFLD,C57BL/6 mice were fed a high fat diet(HFD)for 8 wk,and AML-12 cells were treated with 200μM palmitate acid for 24 h.For AITC treatment,mice were administered AITC(100 mg/kg/d)orally and AML-12 cells were treated with AITC(20μmol/L).RESULTS AITC significantly ameliorated HFD-induced weight gain,hepatic lipid accumulation and inflammation in vivo.Furthermore,serum alanine aminotransferase and aspartate aminotransferase levels were markedly reduced in AITC-treated mice.Mechanistically,AITC significantly downregulated the protein levels of sterol regulatory elementbinding protein 1(SREBP1)and its lipogenesis target genes and upregulated the levels of proteins involved in fatty acidβ-oxidation,as well as the upstream mediators Sirtuin 1(Sirt1)and AMPactivated protein kinaseα(AMPKα),in the livers of HFD-fed mice.AITC also attenuated the nuclear factor kappa B(NF-κB)signaling pathway.Consistently,AITC relieved palmitate acid-induced lipid accumulation and inflammation in AML-12 cells in vitro through the Sirt1/AMPK and NF-κB signaling pathways.Importantly,further studies showed that the curative effect of AITC on lipid accumulation was abolished by siRNA-mediated knockdown of either Sirt1 or AMPKαin AML-12 cells.CONCLUSION AITC significantly ameliorates hepatic steatosis and inflammation by activating the Sirt1/AMPK pathway and inhibiting the NF-κB pathway.Therefore,AITC is a potential therapeutic agent for NAFLD.

关键词： allyl isothiocyanate Nonalcoholic fatty liver disease Hepatic steatosis Liver inflammation

Palladium-Catalyzed Three-Component Coupling Reaction of allyl Carboxylates, Norbornenes and Diboronates InvoIving Sequential Olefins Insertion and Borylation Reaction

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Chinese Journal of Chemistry 2019年第2期37卷 140-147页

作者： Zun Li Jia Zheng Chunsheng Li Wanqing Wu Huanfeng Jiang Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouGuangdong 510640China

Summary of main observation and conclusion An efficient Pd-catalyzed three-component coupling reaction of allyl carboxylates, norbornenes and diboronates is described, which allows efficient assembly of C(sp3)-C(sp3) and C(sp3)-B bonds in a single process. Moreover, this approach shows advantages of good chemo- and regioselectivity, as well as good substrates suitability.

关键词： Palladium-Catalyzed Three-Component Coupling Reaction allyl Carboxylates

A mechanistic study on the regioselective Ni-catalyzed methylation–alkenylation of alkyne with AlMe3 and allylic alcohol

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Organic Chemistry Frontiers 2022年第1期9卷 163-172页

作者： Jiao Liu Deguang Liu Wan Nie Haizhu Yu Jing Shi Hefei National Laboratory for Physical Sciences at the Microscale iChEMCAS Key Laboratory of Urban Pollutant ConversionAnhui Province Key Laboratory of Biomass Clean EnergyDepartment of ChemistryUniversity of Science and Technology of ChinaHefeiAnhui 230026China Department of Chemistry Anhui UniversityHefeiAnhui 230026China

The recently reported Ni-catalyzed methylation–allylation of alkynes with allylic alcohols and AlMe3 reagents delivers valuable tetrasubstituted alkene units in a highly regioselective fashion.Motivated by the experimental significance and the mechanistic ambiguity(e.***.the details of C–O bond activation,the function of the Lewis acid AlMe3,etc.),we conducted a detailed mechanistic study using density functional theory(DFT)calculations.The reaction was found to occur via the C–O bond activation of allylic alcohol,allylation of alkyne,transmetalation,reductive elimination and catalyst regeneration steps.AlMe3 could easily react with the allylic alcohol to form a cyclodialuminoxane species bearing two groups of Lewis acid–base interactions.In this regard,the C(allyl)–O bond is remarkably activated,resulting in a relatively facile C–O activation(compared to the typical Lewis-acid mediated reactions).In addition,the Al–Me interaction is a double-edged sword to the methylation step:the cyclodialuminoxane group functions as the methyl resource,while the full dissociation of the Al–Me interaction(via a cis-to-trans isomerization)is a requisite to fully release the methyl group.In this context,the“Me-relay”pathway involving the[Ni]–Me intermediate is found to be more plausible than all other mechanistic possibilities(such as the typical concerted Me-transfer mechanism in previous studies).

关键词： alcohol catalyzed allyl

NMR Studies of η~3-allyl Rare Earth Metal Complexes

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Journal of Rare Earths 1994年第2期12卷 142-145页

作者：李凤富金鹰泰任吉民孙玉芳裴奉奎王佛松 Acad Sinica Changchun China

The 1H and 13C-NMR spectra of Li(nL)·Ln(η3-C3H5), (Ln = La, n = 3, Ln = Y, n =2.5.Ln = Ce, Pr, Nd, Sm, n = 2, L =dioxane) are reported. The allyl ligands coordinated to rare earth metal ions in every complex are equivalent and delocalized showing n3-allyl character and give strong paramagnetic shifts except the La and Y complexes. The induced shifts of rare earth ions at the allyls were observed and separated .

关键词： Rare earth complex allyl NMR Coordination structure

The Application of allyl as a Protecting Group in the Preparation Of Dinucleoside Carbonate

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Chinese Chemical Letters 1998年第9期9卷 791-793页

作者： Ying ZHOU Liang Ren ZHANG Li He ZHANG (National Laboratory of Natural and Biomimetic Drugs, Beijing Medical University,Beijing 100083) Natl. Lab. of Nat./Biomimetic Drugs Beijing Medical University Beijing 100083 China

Reaction of 5'-O-p-methoxytritylthymidine with 1,1'-carbonyl-diimidazole gave the 3'-O-carbonylimidazolide, which was condensed in high yield with 3'-O-protected thymidine to give a dinucleoside carbonate. In the synthesis of dinucleoside carbonate, allyl can be used as a good protecting group for 3'-hydroxyl of thymidine. The condition of deprotection will not affect the carbonate bridges.

关键词： allyl PdCl2 deprotection dinucleoside carbonate synthesis

Iridium(Ⅲ)-catalyzed two-fold C-H alkylation of BINOLs with allyl alcohols

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Organic Chemistry Frontiers 2022年第2期9卷 471-475页

作者： Hao Liu Wei Chi Meng-Ling Lin Lin Dong Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial TechnologyWest China School of PharmacySichuan UniversityChengdu 610041China

Ir(Ⅲ)-Catalyzed C-H alkylation of BINOL units has been well examined by using allyl alcohols as coupling partners.Under the advantage of the pyridine guiding group,the efficient protocol allows the rapid synthesis of... 详细信息

关键词： alcohols allyl