Indium‐Catalyzed Cycloisomerizations of Cyclopropene‐3,3‐Dicarbonyl Compounds: Efficient Access to Benzo‐Fused Heteroaromatics and Heterobiaryls

Phun, Lien H.; Aponte-Guzman, Joel; France, Stefan

doi:10.1002/ange.201107717

Cited by 8 publications

(1 citation statement)

References 51 publications

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“…2012 年, France 教授课题组用 3,3-二羰基环丙烯在 Lewis 酸 In 的催化下高效地合成了苯并或二苯并杂环化合物 [30] (图 33). 大的影响, 且该反应也为重要有机合成中间体 1,3-二烯化合物的合成提供了新方法 [33] .…”

Section: 非金属卡宾参与的环丙烯开环unclassified

Recent Advances of Cyclopropene Chemistry

Song¹,

Wang²,

Xu³

2015

Acta Chim. Sinica

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Cyclopropenes are the smallest unsaturated carbocyclic but readily accessible compounds with high strain energy (54.1 kcal/mol), which resulting in the high activity of cyclopropenes in reactions. Cyclopropenes have been a hot research topic for many years, since the synthesis, transformations, and applications of cyclopropenes have drawn attentions of chemists, and a series of interesting and significant cyclopropene chemistry have been demonstrated. Especially when transition-metal-catalysts were introduced into cyclopropene chemistry, a number of unprecedented transformations through addition reactions, cycloadditions, and ring-opening reactions have been developed. Several excellent reviews focused on transition metal chemistry of cyclopropenes and enantiomerically enriched cyclopropene have been published before 2011. However, some very important progresses on cyclopropene chemistry have been achieved in the next several years. This review will cover the literatures from 2011 to 2015, including the synthesis, transformations and applications of cyclopropenes. The paper included five chapters: the first part is the introduction of the article; in the second chapter, the recent advances in preparation of cyclopropenes were described; next, in the third part, the recent progress of transformations of cyclopropenes was discussed. The reactions of cyclopropenes were devided into two categories: 1) the transformations in which the ring of cyclopropene was opened by cycloaddition and cycloisomerization reactions. In some reactions an unsaturated metal carbene mechanism was involved, and subsequent insertion reaction, isomerization, or coupling reactions led to diverse functionalized products. In these reactions, cyclopropene serves as a very important 3-carbon building block; 2) the chemical transformations in which the three-membered ring was retained is an important pathway to multisubsitituted cyclopropane derivatives; the forth part summarized the recent applications of cyclopropenes, mainly focused on its specialities as bioorthogonal chemical reporters. Cyclopropene showed great significances in affinity-based protein labeling and synthesis of photo-cross-linkers suitable for live-cell imaging; in the last part, we summed up the article and made an outlook on the future development of cyclopropene chemistry.

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Section: 非金属卡宾参与的环丙烯开环unclassified

Recent Advances of Cyclopropene Chemistry

Song¹,

Wang²,

Xu³

2015

Acta Chim. Sinica

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Cyclopropenes for the Synthesis of Cyclopropane‐Fused Dihydroquinolines and Benzazepines

et al. 2015

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An efficientm ethod for the construction of cyclopropane-fused dihydroquinolines was established by an ovel Povarov-type three-component reaction of aromatic aldehydes,a nilines and cyclopropenesi nt he presence of trifluoromethanesulfonic acid. Ther eactionp roceeded in ar egioselective and diastereoselective manner. Furthermore,t he dihy-droquinolines were smoothly converted to benzazepine derivatives via ar ing opening/isomerization sequence,furtherexpanding the synthetic scope. Results and DiscussionInitially,t he cycloaddition reactiono fb enzaldehyde (4a), aniline (5a), and cyclopropene (6a)w as chosen as the model reaction( Table1). Because of the adverse effect of water, the reactionw as carriedo ut in

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A Catalytic Diastereoselective Formal [5+2] Cycloaddition Approach to Azepino[1,2‐a]indoles: Putative Donor–Acceptor Cyclobutanes as Reactive Intermediates

2014

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A catalytic formal [5+2] cycloaddition approach to the diastereoselective synthesis of azepino[1,2‐a]indoles is reported. The reaction presumably proceeds through a Lewis acid catalyzed formal [2+2] cycloaddition of an alkene with an N‐indolyl alkylidene β‐amide ester to form a donor–acceptor cyclobutane intermediate, which subsequently undergoes an intramolecular ring‐opening cyclization. Azepine products are formed in up to 92 % yield with high degrees of diastereoselectivity (up to 34:1 d.r.).

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Indium‐Catalyzed Cycloisomerizations of Cyclopropene‐3,3‐Dicarbonyl Compounds: Efficient Access to Benzo‐Fused Heteroaromatics and Heterobiaryls

Cited by 8 publications

References 51 publications

Recent Advances of Cyclopropene Chemistry

Recent Advances of Cyclopropene Chemistry

Cyclopropenes for the Synthesis of Cyclopropane‐Fused Dihydroquinolines and Benzazepines

A Catalytic Diastereoselective Formal [5+2] Cycloaddition Approach to Azepino[1,2‐a]indoles: Putative Donor–Acceptor Cyclobutanes as Reactive Intermediates

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