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亲核叔膦促进的联烯酸酯环加成反应研究进展 被引量:12
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作者 杨丽军 马军安 《化学学报》 SCIE CAS CSCD 北大核心 2016年第2期130-148,共19页
20世纪90年代中期,陆熙炎教授报道了亲核叔膦促进的联烯酸酯与缺电子烯烃和亚胺环加成反应.二十年来,作为高效构建功能化碳环及杂环化合物方法,叔膦促进的联烯酸酯环加成反应的发展和应用受到化学家的广泛关注.多样性的亲核叔膦和不同... 20世纪90年代中期,陆熙炎教授报道了亲核叔膦促进的联烯酸酯与缺电子烯烃和亚胺环加成反应.二十年来,作为高效构建功能化碳环及杂环化合物方法,叔膦促进的联烯酸酯环加成反应的发展和应用受到化学家的广泛关注.多样性的亲核叔膦和不同结构联烯酸酯的引入,可呈现多种类型的环加成反应.特别是手性叔膦的应用,高选择性地实现了对该类反应的不对称催化,为一些天然产物和药物模块的全合成开辟了新途径.此外,醛酮化合物也被运用到此类反应中,构建了多种有用的含氧杂环.本篇综述包括六部分:第一部分是引言,概括介绍陆氏反应;第二至五部分分别阐述了亲核叔膦促进联烯酸酯与缺电子烯烃、亚胺、醛酮以及特定亲核试剂的各种环加成反应;最后一部分是总结与展望. 展开更多
关键词 亲核叔膦 联烯酸酯 环加成反应 陆氏反应 两性离子中间体
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Double[3+2] cycloaddition of nitrile oxides with allenoates:Synthesis of spirobidihydroisoxazoles
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作者 Wei Sun Feng Jiang +4 位作者 Honglei Liu Xing Gao Hao Jia Cheng Zhang Hongchao Guo 《Chinese Chemical Letters》 SCIE CAS CSCD 2019年第2期363-366,共4页
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 excelle... 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. 展开更多
关键词 CYCLOADDITION allenoate NITRILE OXIDE SPIROCYCLIC heterocyle
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1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化联烯的[4+2]串联反应:合成苯并噻吩并吡喃衍生物(英文) 被引量:1
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作者 贾继茹 于爱敏 +1 位作者 刘旭光 孟祥太 《有机化学》 SCIE CAS CSCD 北大核心 2019年第8期2175-2182,共8页
发展了1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化硫代橙酮类似物与联烯酸酯之间的串联环化反应,以甲醇为溶剂,以较好的选择性和收率获得两类苯并噻吩并吡喃衍生物.同时,该反应条件温和、底物适应性广,吸电子基或供电子基取代的硫代橙酮类... 发展了1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化硫代橙酮类似物与联烯酸酯之间的串联环化反应,以甲醇为溶剂,以较好的选择性和收率获得两类苯并噻吩并吡喃衍生物.同时,该反应条件温和、底物适应性广,吸电子基或供电子基取代的硫代橙酮类似物都能以较好的选择性和收率生成目标产物.该反应为苯并噻吩并吡喃衍生物的合成提供了一种便利的方法. 展开更多
关键词 串联反应 联烯酸酯 苯并噻吩衍生物
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联烯酯的合成研究进展
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作者 吴阳 郭红超 《化学试剂》 CAS CSCD 北大核心 2013年第12期1085-1088,共4页
总结了近年来经Wittig反应、异构化反应、加成反应、消除反应等途径合成无取代、2-取代、4-取代和多取代2,3-二烯酸酯的合成方法。
关键词 联烯酯 合成 WITTIG反应 异构化反应 加成反应 消除反应
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Copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters for synthesis of functionalized 2,3-allenoates
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作者 Qi Li Zi-Lu Wang Yun-He Xu 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第9期151-155,共5页
Herein,copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters have been developed.The enynic orthoesters as precursors of unstable enynic esters were applied to produce the functionalized 2... Herein,copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters have been developed.The enynic orthoesters as precursors of unstable enynic esters were applied to produce the functionalized 2,3-allenoate products.Meanwhile,the asymmetric 1,4-protosilylation of enynic orthoesters with Ph Me2Si-Bpin was also studied.The chiral monopyridine imidazoline ligand was efficient to provide the asymmetric 1,4-protosilylation products with high enantioselectivity. 展开更多
关键词 COPPER-CATALYZED 1 4-Protosilylation 1 4-Protoborylation 2 3-allenoate Enynic orthoesters
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Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4-1-2] Annulation of α-Substituted Allenoates
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作者 Rongshun Chen Xia Fan +1 位作者 Zhaozhong Xu Zhengjie He 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2017年第9期1469-1473,共5页
A phosphine-catalyzed [4+2] annulation of a-substituted allenoate with exocyclic alkene moiety of oxindoles or indan-1,3-diones has been developed. Thus, under the catalysis of PPh3 (20 mol%), a series of spirooxin... A phosphine-catalyzed [4+2] annulation of a-substituted allenoate with exocyclic alkene moiety of oxindoles or indan-1,3-diones has been developed. Thus, under the catalysis of PPh3 (20 mol%), a series of spirooxindole- or spiroindan-1,3-dione-cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of a-methyl allenoates with 3-methyleneoxindoles or 2-methyleneindan-1,3-diones. This method offers an easy access to structurally novel spirocyclohexenes. 展开更多
关键词 [4+2] annulation reaction phosphine catalysis spirocyclohexenes allenoateS synthesis
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N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones
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作者 孙利辉 王统 叶松 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第1期190-194,共5页
In contrast with the reported phosphine- and DABCO-catalyzed [3 + 2] and [2 +2] annulation of allenoates with trifluoromethylketone, the [2+2+2] annulation of allenoates and two molecules of trifluoromethylketone ... In contrast with the reported phosphine- and DABCO-catalyzed [3 + 2] and [2 +2] annulation of allenoates with trifluoromethylketone, the [2+2+2] annulation of allenoates and two molecules of trifluoromethylketone was found under the condition of N-heterocyclic carbene catalysis. 展开更多
关键词 NHC-catalyzed [2 2 2] annulations allenoateS trifluoromethylketones
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Enantioselective[3 t 2]cycloadditions of terminal allenoates withβ-sulfonyl-α,β-unsaturated ketones
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作者 Xiuzheng Li Jun Liao +4 位作者 Xiaobin Zhuo Huamin Wang Xiaoyun Chai Yan Zou Qingjie Zhao 《Green Synthesis and Catalysis》 2023年第1期54-57,共4页
A highly efficient and mild method for[3 t 2]cycloaddition ofβ-sulfonyl-α,β-unsaturated ketones with terminal allenoates was well-explored and developed.The reactions were successfully performed by applying multifu... A highly efficient and mild method for[3 t 2]cycloaddition ofβ-sulfonyl-α,β-unsaturated ketones with terminal allenoates was well-explored and developed.The reactions were successfully performed by applying multifunctional chiral phosphine P6 which was screened from eight chiral phosphorus reagents to finally result in a variety of enantioenriched sulfone-substituted cyclopentenes with two chiral centers(up to 81%yield with 94%ee).Moreover,2.5 mol%catalytic equivalents were proved to be feasible when this reaction was performed on a 10 mmol scale. 展开更多
关键词 [3t2]Cycloadditions Terminal allenoates α β-Unsaturated ketones ENANTIOSELECTIVE Chiral phosphine
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Recent advances in tertiary amine Lewis base-promoted cycloadditions of allenoates 被引量:1
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作者 Manman Song Jing Zhao Er-Qing Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第5期2372-2382,共11页
Lewis base-catalyzed annulations of allenoates have been one of the most powerful synthetic strategies for the synthesis of various valuable cycles,especially in the preparation of biologically active natural products... Lewis base-catalyzed annulations of allenoates have been one of the most powerful synthetic strategies for the synthesis of various valuable cycles,especially in the preparation of biologically active natural products and pharmaceuticals.Generally,the effective Lewis bases mainly include tertiary phosphine,NHC and tertiary amine catalysts,among those catalysis,tertiary amine Lewis bases have proven to be effective catalysts for a range of synthetic transformations.In the past decades,tremendous progress in-volving tertiary amines-promoted cycloaddition of allenoates has been made in the chemoselective con-struction of valuable motifs.This review describes a comprehensive and updated summary of tertiary amine Lewis base-promoted annulation reactions of allenoates.Diverse reactivities,chemoselectivties and detailed reaction mechanisms will be highlighted in this review. 展开更多
关键词 Lewis base Tertiary amine Annualtion allenoateS OLEFIN
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Enantioselective synthesis of mixed 3,3’-bisindoles via a phosphine-catalyzed umpolung γ-addition of 3’-indolyl-3-oxindoles to allenoates 被引量:1
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作者 Yildiz Tasdan Guang-Jian Mei Yixin Lu 《Science Bulletin》 SCIE EI CAS CSCD 2020年第7期557-563,M0004,共8页
An enantioselective umpolung γ-addition reaction of 3’-indolyl-3-oxindoles to allenoates catalyzed by amino acid-derived bifunctional phosphine catalysts has been developed. A wide range of chiral mixed 3,3’-bisind... An enantioselective umpolung γ-addition reaction of 3’-indolyl-3-oxindoles to allenoates catalyzed by amino acid-derived bifunctional phosphine catalysts has been developed. A wide range of chiral mixed 3,3’-bisindole scaffolds containing an all-carbon quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities. 3,3’-Bisindoles are valuable synthetic intermediates, the employment of which led to formal total syntheses of(+)-Chimonanthine,(+)-Folicanthine and(-)-Calycanthine, as well as facile creation of useful pyrrolidinoindoline core structure. 展开更多
关键词 Umpolung c-addition Amino acid-derived bifunctional phosphine allenoateS Mixed 3 30-Bisindole Formal total syntheses
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Assembly of 3-sulfonated 2H-pyrrol-2-ones through the insertion of sulfur dioxide with allenoic amides
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作者 Kaida Zhou Jianqiang Chen Jie Wu 《Chinese Chemical Letters》 SCIE CAS CSCD 2020年第12期2996-2998,共3页
Generation of 3-sulfonated 2 H-pyrrol-2-ones through a three-component reaction of allenoic amides,sulfur dioxide,and aryldiazonium tetrafluoroborates under metal-free conditions is achieved.This transformation procee... Generation of 3-sulfonated 2 H-pyrrol-2-ones through a three-component reaction of allenoic amides,sulfur dioxide,and aryldiazonium tetrafluoroborates under metal-free conditions is achieved.This transformation proceeds under mild conditions without the addition of catalysts or additives,giving rise to 3-sulfonated 2 H-pyrrol-2-ones in moderate to good yields.Good functional group compatibility is observed.A plausible mechanism is proposed,which is initiated by aryl radicals formed in situ from aryldiazonium tetrafluoroborates and DABCO·(SO2)2.Additionally,excellent chemoselectivity and regioselectivity are presented in this transformation. 展开更多
关键词 allenoic amide Aryldiazonium tetrafluoroborate 3-Sulfonated 2H-pyrrol-2-one Sulfur dioxide METAL-FREE
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Direct Double Electrophilic Fluorination of Allenoic Acids and Tosylamides to Give 1,1-Difluoroallylic Heterocyclic Compounds 被引量:1
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作者 崔海峰 柴卓 +3 位作者 陆颖鹏 李鹏 赵刚 朱士正 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第12期2744-2748,共5页
A novel and facile preparation of l,l-difluoroallyl substituted five-membered lactones or pyrrolidines in mod- erate yields through direct double electrophilic fluorination of 4,5-allenoic acids or tosylamides with Se... A novel and facile preparation of l,l-difluoroallyl substituted five-membered lactones or pyrrolidines in mod- erate yields through direct double electrophilic fluorination of 4,5-allenoic acids or tosylamides with SelectfluorTM F-TEAD-BF4 is described. 展开更多
关键词 SELECTFLUOR electrophilic fluorination 4 5-allenoic acid 4 5-allenoic tosylamide allyl difluoride
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过渡金属催化的2,3-联烯酸环化合成γ-丁烯酸内酯(英文) 被引量:3
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作者 麻生明 俞瞻前 《中国科学院研究生院学报》 CAS CSCD 2005年第1期110-121,共12页
γ 丁烯酸内酯是一类具有重要潜在活性的化合物 .发展了二价钯催化的 2 ,3 联烯酸和 (ω 1 ) 烯基卤化物的偶联关环反应 .反应经过了二价钯催化的氧钯化 碳钯化 ,重复的去钯氢化 钯氢化及 β 脱卤钯化反应 .同时还发展了两种联烯之间... γ 丁烯酸内酯是一类具有重要潜在活性的化合物 .发展了二价钯催化的 2 ,3 联烯酸和 (ω 1 ) 烯基卤化物的偶联关环反应 .反应经过了二价钯催化的氧钯化 碳钯化 ,重复的去钯氢化 钯氢化及 β 脱卤钯化反应 .同时还发展了两种联烯之间的二聚环化反应 ,两分子 2 ,3 联烯酸的反应生成二丁烯酸内酯 ,2 ,3 联烯酸与 1 ,2 联烯酮反应则生成呋喃基取代的γ 丁烯酸内酯 . 展开更多
关键词 过渡金属 催化 2 3-联烯酸 环化合成 γ-丁烯酸内酯 氧化
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Dramatic Solvent Effect in the Reduction of 2,3-Allenoic Acid Esters. A Simple Synthesis of 2,3-Allenols from 2,3-Allenoates
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作者 尹少虎 麻生明 +1 位作者 焦宁 陶凤岗 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2002年第7期707-710,共4页
2,3-Allenols were prepared conveniently from the reduction reaction of 2, 3-allenoates with DIBAL-H (Diisobutylaluminum hydride) in toluene. A dramatic solvent effect was observed for this reaction.
关键词 2 3-allenoates REDUCTION 2 3-allenols
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有机磷催化γ-甲基联烯酸酯[3+2]环化反应 被引量:1
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作者 马蓉 宋格格 +3 位作者 奚秋贞 杨柳 李二庆 段征 《有机化学》 SCIE CAS CSCD 北大核心 2019年第8期2196-2202,共7页
在有机磷催化下,γ-甲基联烯酸酯和烯基茚二酮经过[3+2]环加成反应,以中等到较好的产率、高化学选择性和非对映选择性形成一系列官能团化的螺环化合物.该反应具有操作简单、反应条件温和和底物适用性广等优点.需要指出的是,使用简单易得... 在有机磷催化下,γ-甲基联烯酸酯和烯基茚二酮经过[3+2]环加成反应,以中等到较好的产率、高化学选择性和非对映选择性形成一系列官能团化的螺环化合物.该反应具有操作简单、反应条件温和和底物适用性广等优点.需要指出的是,使用简单易得的PPh3作为催化剂,就能实现完全的α-区域选择性加成的环化产物. 展开更多
关键词 有机磷催化 γ-甲基联烯酸酯 [3+2]环化反应
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