25364-76-5Relevant academic research and scientific papers
Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis
Wei, Xu,Lu, Junzhu,Duan, Wei-Liang
, p. 4155 - 4160 (2016)
A pincer-palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to allylidenemalonates has been developed for the synthesis of chiral allylic phosphines with up to 89% ee under mild conditions.
Tellurium-Assisted Cycloprpanation and Alkylidenation of α,β-Unsaturated Carbonyl Compounds with Dibromomalonic Esters
Matsuki, Toshiaki,Hu, Nan Xing,Otsubo, Tetsuo,Ogura, Fumio
, p. 2105 - 2107 (1989)
Dibutyl telluride assists cyclopropanation of α,β-unsaturated ketone, ester, and nitrile with dibromomalonic esters without solvent at room temperature.In addition, it effects alkylidenation of aldehydes including α,β-unsaturated aldehyde with the same reagent.
Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations
Delbrassinne, Arnaud,Richald, Maximilien,Janssens, Julien,Robiette, Rapha?l
supporting information, p. 2862 - 2868 (2021/06/11)
Vinylcyclopropanes are versatile intermediates in organic synthesis which undergo various rearrangements. We report a new rearrangement of vinylcyclopropane into skipped diene. A detailed mechanistic study revealed that this transformation involves regioselective ring-opening of the cyclopropane ring followed by 1,2-migration of one of the cyclopropane substituents. Interestingly, our investigations showed that skipped diene is the kinetic product of the process but formation of a more stable cyclopentene is also accessible. The fundamental understanding of the processes involved enabled the development of divergent methodologies allowing to obtain cyclopentene or skipped diene from vinylcyclopropane in a selective and controlled manner.
Copper-catalyzed regiodivergent 1,4-and 1,6-conjugate silyl addition to diendioates: Access to functionalized allylsilanes
Ahmad, Tanveer,Li, Qi,Qiu, Sheng-Qi,Xu, Jian-Lin,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 6122 - 6126 (2019/07/03)
A copper-catalyzed regioselective 1,4-and 1,6-conjugate addition of a silyl reagent to diendioates was established. Various 1,4-and 1,6-protosilylation products were obtained in good yields and with high regioselectivity via tuning the ligands used in the reactions. This protocol has provided a simple and efficient method for the synthesis of multisubstituted functionalized allylsilanes.
Ring-Opening of Vinylcyclopropane-1,1-dicarboxylates by Boronic Acids under Ligandless Palladium Catalysis in Neat Water
Yin, JieXiang,Hyland, Christopher J. T.
, p. 6529 - 6536 (2015/10/06)
We report a highly efficient ring-opening reaction of vinylcyclopropanes by boronic acids in water, using palladium nanoparticles formed from Pd(OAc)2 under ligandless conditions. Unsubstituted vinylcyclopropanes provide linear addition products with high selectivity, while a switch in regioselectivity to branched products is observed for aryl-substituted vinylcyclopropanes.
Organocatalytic asymmetric annulation of 1,3-bis(alkoxycarbonyl)buta-1,3- dienes and aldehydes
Pezzati, Bernardo,Chellat, Mathieu F.,Murphy, John J.,Besnard, Celine,Reginato, Gianna,Stephens, John C.,Alexakis, Alexandre
supporting information, p. 2950 - 2953 (2013/07/26)
Asymmetric organocatalytic annulation of E/Z isomeric mixtures of bis(alkyl carboxylate)buta-1,3-dienes and aldehydes has been realized via enamine catalysis. In the presence of α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether, excellent stereo- and enantioselectivities were achieved for a broad spectrum of substrates.
Asymmetric michael addition of ketones to alkylidene malonates and allylidene malonates via enamine - Metal lewis acid bifunctional catalysis
Liu, Lu,Sarkisian, Ryan,Xu, Zhenghu,Wang, Hong
supporting information, p. 7693 - 7699 (2012/11/07)
Novel enamine-metal Lewis acid bifunctional catalysts were successfully applied to the asymmetric Michael addition of ketones to alkylidene malonates, offering excellent stereoselectivity (up to >99% ee and >99:1 dr). The asymmetric Michael addition of ketones to allylidene malonates was also achieved.
Natural α-amino acid l-lysine-catalyzed knoevenagel condensations of α,β-unsaturated aldehydes and 1,3-dicarbonyl compounds
He, Yan-Hong,Hu, Ying,Guan, Zhi
experimental part, p. 1617 - 1628 (2011/06/21)
Knoevenagel condensations of α,β-unsaturated aldehydes and 1,3-dicarbonyl compounds were catalyzed by primary natural amino acid L-lysine. The reactions were carried out at room temperature in dimethylsulfoxide. It provides a facile entry to a wide variety of α,β,γ,δ- unsaturated dicarbonyl compounds. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
A dimethylsulfonium methylide mediated highly regioselective olefination of conjugated polyolefin 1,1-dioates to conjugated polyene-2-yl-malonates and their applications in Diels-Alder reactions
Singh, Rekha,Ghosh, Sunil K.
supporting information; experimental part, p. 2284 - 2292 (2010/06/16)
The reactions between dimethylsulfonium methylide and 1,3-diene- or 1,3,5-triene-1,1-dioates under specific conditions enable the highly regioselective tandem ylide addition-eliminative olefination to provide 1,3-butadien-2-yl- or 1,3,5-hexatriene-2-yl-malonates. Alkylation at malonate methine carbon of 1,3-butadien-2-ylmalonates with a suitable alkyl halide having in-built functionalities for a dienophile generation led to quick assembly of precursors for type 2 intramolecular Diels-Alder reaction. Syntheses of functionalized bicyclo[n.3.1] alkenes (n=5 or 6) with the double bond at the bridgehead position have been achieved via the IMDA. An asymmetric version of this reaction has been developed using a MacMillan's imidazolidinone catalyst, which provided a bicyclo[5.3.1] alkene with very high enantioselectivity. In situ methylation at malonate methine carbon of 1,3,5-hexatriene-2-yl-malonates followed by intermolecular Diels-Alder reaction with N-methylmaleimide provided the cycloadduct with complete regiocontrol and high diastereoselectivity.
A nBuLi-mediated, expeditious and stereoselective ring-opening rearrangement of (arylmethylene)cyclopropane-1,1-dicarboxylates
Hu, Bao,Jiang, Linan,Ren, Jun,Wang, Zhongwen
experimental part, p. 1358 - 1363 (2010/04/29)
We report herein an nBuLi-mediated, expeditious, ring-opening rearrangement of (arylmethylene)cyclopropane 1,1-diesters to prepare 1,3-diene derivatives with good stereo-selectivity. The reaction mechanism has also been discussed.
