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Benito Alcaide Pedro Almendros Israel Fernndez Teresa Martínez del Campo Teresa Naranjo 《Advanced Synthesis \u0026amp; Catalysis》2013,355(13):2681-2685
α‐Allenols were catalytically transformed into dihydrofurans in the presence of platinum dichloride. Notably, using platinum dichloride along with silver triflate as the catalytic system, α,β‐unsaturated ketones were obtained. Therefore, the role of the silver salt may not just consist in the activation of the platinum precatalyst.
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Herein a practical and efficient protocol for preparing a range of aminoisoquinolines is reported. Various aminoisoquinolines were prepared in moderate to good yields from the corresponding 2‐methylbenzonitriles and benzonitriles upon treatment with potassium tert‐butoxide.
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Simon Allmendinger Hirotaka Kinuta Bernhard Breit 《Advanced Synthesis \u0026amp; Catalysis》2015,357(1):41-45
The synthesis of chiral bidentate bisphosphonite ligands based on the TADDOL motif from readily available starting materials has been developed. Taking advantage of the modular nature of the building blocks, a diverse ligand library has been prepared. Their catalytic potential has been evaluated in the asymmetric hydroformylation of styrene and derivatives. These catalysts showed high activity and provided the aldehydes in high enantiomeric purity.
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Ryo Watari Yoshihito Kayaki Shin‐ichi Hirano Norio Matsumoto Takao Ikariya 《Advanced Synthesis \u0026amp; Catalysis》2015,357(7):1369-1373
Hydrogenation of carbon dioxide to formate was achieved using copper (Cu) catalysts in the presence of strong organic bases including amidines and guanidines. Specifically, 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) proved to be effective for the transformation of a 1:1 mixture of hydrogen and carbon dioxide into its formate salt under increased pressure in the presence of various Cu(I) and Cu(II) salts at 100 °C. A novel complex derived from copper iodide and DBU equally promoted the same reaction, indicating that DBU–Cu species are involved as real catalysts in this hydrogenation.
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Hong‐Wu Zhao Hai‐Liang Pang Ting Tian Bo Li Xiao‐Qin Chen Xiu‐Qing Song Wei Meng Zhao Yang Yue‐Yang Liu Yu‐Di Zhao 《Advanced Synthesis \u0026amp; Catalysis》2016,358(11):1826-1832
In the presence of sodium carbonate, the [4+3] cycloadditions of α‐halogeno hydrazones with nitrones were performed efficiently, and affording 2,3,4,7‐tetrahydro‐1,2,4,5‐oxatriazepines in moderate to high yields.
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Junyu Xu Shihe Hu Yingyan Lu Ying Dong Weifang Tang Tao Lu Ding Du 《Advanced Synthesis \u0026amp; Catalysis》2015,357(5):923-927
A novel synthetic method to access fused indolin‐3‐ones with a tetrasubstituted carbon stereocenter has been developed via NHC‐catalyzed umpolung formal [3+3] cycloaddtion of enals with isatogens. This methodology could be also applied for the quick construction of the 6‐5‐5 tricyclic pyrrolo[1,2‐a]indole skeleton which is frequently found as a core structure of many indole alkaloids.
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Seong Jong Lee Hong‐Ahn Seo Cheol‐Hong Cheon 《Advanced Synthesis \u0026amp; Catalysis》2016,358(10):1566-1570
A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino‐Stetter reaction of aldimines obtained from 2‐aminocinnamic acid derivatives and aromatic aldehydes with cyanide, affording 2‐aryl‐substituted indole‐3‐acetic acid derivatives. Furthermore, the usefulness of this method was successfully demonstrated by the synthesis of an FPTase inhibitor, one of the biologically important 2‐arylindole‐3‐acetic acid derivatives.
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Naganaboina Naveen Srinivasa Rao Koppolu Rengarajan Balamurugan 《Advanced Synthesis \u0026amp; Catalysis》2015,357(7):1463-1473
A practically simple and direct α‐alkylation of unactivated ketones using benzylic alcohols has been achieved. The in situ formed acetals are the key for the success of the reaction. The catalyst, silver hexafluoroantimonate(V) (AgSbF6) provides double activation by converting the ketone into an enol ether via acetal and generation of carbocationic center at the benzylic position of the benzylic alcohol. The alcohols include benzylic propargyl alcohols, cinnamyl alcohols, and diarylmethanols.
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Sergey Vshyvenko Zemane W'Giorgis Audrey Weber Natalia Neverova Bradley Hedberg Tomas Hudlicky 《Advanced Synthesis \u0026amp; Catalysis》2015,357(1):83-87
The first active aza analogue of narciclasine was synthesized from a pentasubstituted derivative of nicotinic acid. The key features of the synthesis include a halogen dance of bromopyridine and an intramolecular Heck reaction with a conduramine derived chemoenzymatically from bromobenzene. 10‐Aza‐narciclasine was found to have reasonable activity against several cancer cell lines.
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You‐Qing Wang Yongna Zhang Kun Pan Junxiong You Jin Zhao 《Advanced Synthesis \u0026amp; Catalysis》2013,355(17):3381-3386
3‐Substituted‐2H‐1,4‐benzoxazines undergo a highly enantioselective direct Mannich reaction with acetone in the presence of an L ‐proline catalyst at room temperature. The corresponding N‐heterocycles with α‐tetrasubstituted carbon stereocenters were obtained in good yields (48–92%) and excellent enantioselectivity (up to >99% ee). Furthermore, a novel modification involving the diastereoselective reduction of the Mannich adduct was carried out leading to the formation of a 1,3‐amino alcohol with a chiral tetrasubstituted carbon stereocenter in high yield.
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Fleur Drouet Jieping Zhu Graldine Masson 《Advanced Synthesis \u0026amp; Catalysis》2013,355(18):3563-3569
The iron(III) chloride‐multicatalyzed dioxygenation of enamides with TEMPO in the presence of alcohols has been developed. This multicomponent domino process affords efficient new strategies for the synthesis of α‐oxy‐N‐acylhemiaminals or α‐oxyimides in good to excellent yields under mild conditions.
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Zinc‐Catalyzed Selective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω‐Hydroxylactams
Guangni Ding Bin Lu Yuyuan Li Jun Wan Zhaoguo Zhang Xiaomin Xie 《Advanced Synthesis \u0026amp; Catalysis》2015,357(5):1013-1021
Cyclic imides were selectively reduced to the corresponding ω‐hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2⋅2 H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.
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Michael J. Ardolino Meredith S. Eno James P. Morken 《Advanced Synthesis \u0026amp; Catalysis》2013,355(17):3413-3419
Kinetic resolution during the catalytic allyl‐propargyl cross‐coupling with chiral starting materials can be accomplished with a chiral palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple, readily available starting materials.
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Yu‐Yang Xie Ying‐Chun Wang Hong‐En Qu Xian‐Chun Tan Heng‐Shan Wang Ying‐Ming Pan 《Advanced Synthesis \u0026amp; Catalysis》2014,356(16):3347-3355
A highly regioselective synthesis of β‐aryl enaminones and 1,4,5‐trisubstituted 1,2,3‐triazoles from chalcones and benzyl azides based on reaction solvent selection is reported. In the presence of a catalytic amount of Ce(OTf)3, reactions of chalcones with benzyl azides in DMF at 100 °C afforded densely substituted Z‐β‐aryl enaminones in good to excellent yields, whereas treatment of chalcones with benzyl azides in toluene at 100 °C selectively produced 1,4,5‐trisubstituted 1,2,3‐triazoles in excellent yields.
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Zhiyong Wu Chao Pi Xiuling Cui Jie Bai Yangjie Wu 《Advanced Synthesis \u0026amp; Catalysis》2013,355(10):1971-1976
An efficient and concise one‐pot strategy for the direct alkylation of quinoline N‐oxides via palladium‐catalyzed dual C H bonds activation has been developed. This methodology provides quinoline‐containing heterocyclic molecules in moderate to excellent yields.
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María D. Díaz‐de‐Villegas Jos A. Glvez Ramn Badorrey Pilar Lpez‐Ram‐de‐Víu 《Advanced Synthesis \u0026amp; Catalysis》2014,356(16):3261-3288
Recent progress in asymmetric organocatalysis has led to the development of several asymmetric transformations that employ various substrates. Among these, cyanoacetates have emerged as excellent nucleophiles in conjugate addition, alkylation, Mannich and α‐heterofunctionalization reactions. In this review we discuss the enantioselective functionalization of 2‐cyanoacetates through organocatalytic reactions.