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Lewis Acid Catalyzed Asymmetric Three‐Component Coupling Reaction: Facile Synthesis of α‐Fluoromethylated Tertiary Alcohols 下载免费PDF全文
Dr. Kohsuke Aikawa Daisuke Kondo Kazuya Honda Prof. Dr. Koichi Mikami 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(49):17565-17569
A chiral dicationic palladium complex is found to be an efficient Lewis acid catalyst for the synthesis of α‐fluoromethyl‐substituted tertiary alcohols using a three‐component coupling reaction. The reaction transforms three simple and readily available components (terminal alkyne, arene, and fluoromethylpyruvate) to valuable chiral organofluorine compounds. This strategy is completely atom‐economical and results in perfect regioselectivities and high enantioselectivities of the corresponding tertiary allylic alcohols in good to excellent yields. 相似文献
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Novel One‐Pot Three‐Component Reaction for the Synthesis of Functionalized Spiroquinazolinones 下载免费PDF全文
Mahdieh Tajbakhsh Sorour Ramezanpour Saeed Balalaie Hamid Reza Bijanzadeh 《Journal of heterocyclic chemistry》2015,52(5):1559-1564
A wide variety of spiroquinazolinone derivatives have been synthesized via a one‐pot three‐component reaction of isatoic anhydride, cyclic ketones, and hydrazides in the presence of catalytic amount (20 mol%) of H3PO3 in ethanol. Mild reaction conditions, high atom economy, operational simplicity, and good to high yields are the key advantages of the present protocol. 相似文献
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A direct three‐component approach has been developed for the synthesis of α‐cyano acrylates starting from aldehydes, alcohols and α‐cyano acetamide by employing cyanuric chloride as an organocatalyst. A class of structurally diverse α‐cyano acrylates have been provided with good to excellent yields via the cascade transformation of Knoevenagel condensation and amide esterification. 相似文献
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An environmentally benign and efficient method has been developed for the synthesis of functionalized tetrahydroindole derivatives in aqueous media under catalyst‐free conditions, by simply combining a phenylglyoxal monohydrate, an enaminone, and a barbituric acid. The advantages of this method are that it is catalyst free, has an easy workup, provides good yields, and uses water as solvent, which make this procedure facile and practical. 相似文献
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《中国化学》2017,35(12):1808-1812
A one‐pot three‐component reaction of aldehydes, nitroalkanes and NaN3 for the synthesis of NH ‐1,2,3‐triazoles has been developed. The reaction provides a safe, efficient and step‐economic approach for the synthesis of various NH ‐1,2,3‐triazoles in good to excellent yields. 相似文献
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Faramarz Rostami‐Charati Zinatossadat Hossaini Ebrahim Gharaee Mohammad A. Khalilzadeh 《Journal of heterocyclic chemistry》2013,50(Z1):E174-E177
A one‐pot synthesis of oxazine derivatives via reaction between activated acetylenic compounds, benzoyl cyanide, and N‐nucleophiles in water as the solvent is described?. 相似文献
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The silver(I)‐catalyzed synthesis picture of axially chiral allenes based on propargylamines has been outlined using density functional theory (DFT) method for the first time. Our calculations find that, the coordination of silver(I) into triple bond of propargylamines at anti‐position of nitrogen shows a stronger activation on the triple bond than that at cis‐position, which is favorable for the subsequent hydrogen transfer. The NBO charge analysis for the hydrogen transfer affirms the experimental speculation that this step is a hydride transfer process. The energy barrier of the anti‐periplanar elimination of vinyl‐silver is 26.9 kJ·mol?1 lower than that of the syn‐periplanar elimination, supporting that (?)‐allene is the main product of this reaction. In a word, the most possible route for this reaction is that the silver(I) coordinates into the triple bond of propargylamines at anti‐position of nitrogen, then the formed silver(I) complex undergoes a hydride transfer to give a vinyl‐silver, finally the vinyl‐silver goes through an anti‐periplanar elimination to give (?)‐allene. The hydride transfer with the energy barrier of 44.8 kJ·mol?1 is the rate‐limiting step in whole catalytic process. This work provides insight into why this reaction has a very high enantioselectivity. 相似文献
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Mehdi Adib MohammadHosein Sayahi SomayehAali Koloogani Peiman Mirzaei 《Helvetica chimica acta》2006,89(2):299-303
The reactive 1 : 1 zwitterionic intermediates generated in situ from the reaction between a series of isocyanides and diaroylacetylenes were trapped by pyridine carbaldehydes to yield highly functionalized 5‐pyridylfuran‐2‐amines in good yields (82–93%). 相似文献
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Liyi Tan Daisuke Takeuchi Kohtaro Osakada 《Journal of polymer science. Part A, Polymer chemistry》2019,57(24):2535-2542
The Pd‐catalyzed three‐component coupling polycondensation of diiodoarenes, nonconjugated dienes, and carbonucleophiles afforded poly(arylene alkenylene)s with moderate molecular weight in good yield. The reaction involves Mizoroki‐Heck coupling, olefin migration via chain walking, and addition of the carbonucleophile to the resulting π‐allylpalladium species. The polymerization with a slight excess of nucleophile with respect to diiodoarene also proceeded to give the polymer without significant decrease in molecular weight in spite of the nonstoichiometric mixture of the monomers. The Pd‐catalyzed three‐component coupling polycondensation of diiodoarenes, nonconjugated dienes, and diimide also proceeded. The base used in the reaction is critical for yield and molecular weight of the product. The reaction using NaHCO3 afforded the product with low solubility, which can be explained by the high molecular weight of the polymer and/or the strong interaction of the electron donating dimethoxyphenylene groups and electron accepting diimide groups in the polymer. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019 , 57, 2535–2542 相似文献
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An Efficient Synthesis of Spiro‐oxindole Derivatives by Three‐Component Reactions in Water 下载免费PDF全文
An efficient synthesis of (3S)‐1,1′,2,2′,3′,4′,6′,7′‐octahydro‐9′‐nitro‐2,6′‐dioxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carbonitrile is achieved via a three‐component reaction of isatin, ethyl cyanoacetate, and 1,2,3,4,5,6‐hexahydro‐2‐(nitromethylidene)pyrimidine. The present method does not involve any hazardous organic solvents or catalysts. Also the synthesis of ethyl 6′‐amino‐1,1′,2,2′,3′,4′‐hexahydro‐9′‐nitro‐2‐oxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carboxylates in high yields, at reflux, using a catalytic amount of piperidine, is described. The structures were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS data) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2). 相似文献
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A sequential one‐pot two‐step reaction for efficient synthesis of pyrrolo[2,1‐a]isoquinoline and pyrrolo[1,2‐a]quinoline derivatives in good yields has been successfully developed. The reaction included firstly Cu‐catalyzed three‐component reaction of isoquinoline (quinoline), acetylenedicarboxylate and alkynylbenzene and then Pd‐catalyzed intramolecular C(sp)‐C(sp2) coupling reaction of initially formed 1‐alkenyl‐2‐alkynyl‐1,2‐dihydroisoquinoline (1,2‐dihydroquinoline). 相似文献
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Biswanath Das Rathod Aravind Kumar Ponnaboina Thirupathi 《Helvetica chimica acta》2007,90(6):1206-1210
A simple and efficient method has been developed for the synthesis of α‐amino nitriles from aldehydes, amines and trimethylsilyl cyanide (Me3SiCN) in the presence of a catalytic amount of cyanuric acid at room temperature. 相似文献
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Gaochao Huang Dr. Zengsheng Yin Prof. Dr. Xingang Zhang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(36):11992-11998
A general and efficient method for the highly enantioselective alkynylation of ketoimines through a zinc/1,1′‐bi‐2‐naphthol (BINOL)‐catalyzed process has been developed. A variety of ketoimines, including α‐fluoroalkyl α‐imine esters, α‐aryl α‐imine esters, and trifluoromethyl aryl ketoimines, are applicable and provide their corresponding quaternary propargyl amines in excellent yields with high ee values (up to 99 % ee). Both the steric and electronic effects of substituents at the 3,3′ positions of BINOL are critical for the reaction efficiency and enantioselectivity. To demonstrate the usefulness of the method, (R)‐α‐CF3 α‐proline has been prepared in a highly efficient manner. The notable features of this protocol are its broad substrate scope, high reaction efficiency (up to 99 %) and enantioselectivity (up to 99 % ee), low catalyst loading (5 mol % of BINOL derivative), and mild reaction conditions. 相似文献
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Dr. Gonzalo Blay Ana Brines Alicia Monleón Prof. Dr. José R. Pedro 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(8):2440-2444
Chiral nonracemic N‐Cbz‐protected propargylic amines have been prepared by the addition of terminal alkynes to imines generated in situ from α‐amido sulfones in the presence of diethylzinc and BINOL‐type ligands as catalysts. The reactions give good yields and high enantioselectivities (ee values up to 95 %) for a good number of aromatic and heteroaromatic α‐amido sulfones and alkynes. 相似文献