1160723-52-3Relevant academic research and scientific papers
Enantioselective Rhodium-Catalyzed Hydrogenation of (Z)-N-Sulfonyl-α-dehydroamido Boronic Esters
Li, Zhenya,Xu, Ronghua,Guo, Huichuang,Yang, He,Xu, Guangqing,Shi, Enxue,Xiao, Junhua,Tang, Wenjun
supporting information, p. 714 - 719 (2022/01/20)
Highly enantioselective rhodium-catalyzed hydrogenation of (Z)-N-sulfonyl-α-dehydroamido boronic esters is realized for the first time using a JosiPhos-type ligand. This method has enabled convenient synthesis of a series of enantio-enriched N-sulfonyl-α-amido boronic esters in good yields and excellent enantioselectivities (up to 99% ee).
Metal-Free Hydrophosphoryloxylation of Ynamides: Rapid Access to Enol Phosphates
An, Dalie,Zhang, Weinan,Pan, Bin,Zhao, Yingying
supporting information, p. 314 - 317 (2020/12/11)
We herein report a metal-free hydrophosphoryloxylation of ynamides with phosphoric acids, which provides an expeditious route to access useful enol phosphates. The advantages of this protocol include exclusive selectivity, short reaction time, high efficiency, and broad substrate scope. Additionally, the products can serve as good partners in Suzuki-Miyaura cross-coupling.
Synthesis of dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline through Cu(OTf)2-catalyzed reactions of N-acyliminium ions with ynamides
Ma, Rui-Jun,Xu, Wen-Ke,Sun, Jian-Ting,Chen, Ling,Si, Chang-Mei,Wei, Bang-Guo
supporting information, (2021/02/27)
An efficient approach to access functionalized dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline skeletons has been developed through the addition-cyclization process of ynamides 8 with N-acyliminium ions generated from N,O-acetals 6,7. The reactions were conducted under the catalysis of Cu(OTf)2, and a number of functionalized dihydro-[1,3]oxazino[4,3-a] isoindoles 9a-9y and tetrahydroisoquinolines 10a-10g, 11a-11p were generated in 48–98% yields. When chiral ynamides 8n-8u were used, optically pure products 11a-11p could be obtained with good to excellent yields and diastereoselectivities.
Keteniminium-Driven Umpolung Difunctionalization of Ynamides
Dutta, Shubham,Gandon, Vincent,Mallick, Rajendra K.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 10785 - 10790 (2020/03/13)
A three-component Pd-catalyzed coupling of ynamides, aryl diazonium salts, and aryl boronic acids for the synthesis of novel triaryl-substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsymmetrical syn-1,2-diarylation/aryl-olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α- and nucleophilic β-position, respectively, of the ynamide, resulting in a single isomer of the N-bearing tetrasubstituted olefin. The scope is broad (68 examples), showing excellent functional-group tolerance. DFT calculations substantiate the rationale of the mechanistic cycle and the regioselectivity. The chemoselectivity and synthetic potential of the enamide products were also studied.
Er(OTf)3-catalyzed approach to 3-alkenylindoles through regioselective addition of ynamides and indoles
Liu, Yi-Wen,Ma, Rui-Jun,Si, Chang-Mei,Wang, Qiao-E,Wei, Bang-Guo
, (2020/10/14)
An efficient approach to access functionalized 3-alkenylindoles has been developed through Er(OTf)3-catalyzed addition of ynamides and indoles. A number of C-aryl substituted ynamides 7a-7k could react with indoles 6a-6s, affording the desired products 8aa-8sa, 8ab-8ak, 8bd, 8bk and 8tc in moderate to excellent yields with high regioselectivities.
A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water
Yang, Yunqin,Meng, Xiangtai,Zhu, Baolong,Jia, Ying,Cao, Xiaoji,Huang, Shenlin
, p. 1166 - 1169 (2019/01/04)
Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.
Preparation method of water-phase alkynyl amine compounds and product obtained by preparation method
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Paragraph 0049-0053, (2019/12/25)
The invention relates to a preparation method of alkynyl amine compounds and products obtained by the preparation method, and belongs to the technical field of chemical synthesis. The method comprisesthe following steps: adding a secondary amine compound, copper sulfate pentahydrate, 1,10-phenanthroline and potassium carbonate into a 4 mL reaction flask, adding 2 wt% a surfactant APGS-550-M aqueous phase system, adding alkynyl bromide, performing heating to 50 DEG C, performing continuous stirring at 900-1000 rpm for 26 h, performing extraction for three times by using ethyl acetate, performing rotary evaporation concentration, and performing separation by using silica gel column chromatography to obtain the products. The method provided by the invention can be used for derivation of natural products and synthesis of drug structures; and the method has the following advantages: 1) water is used for replacing an organic solvent, so that the environmental pollution is reduced; 2) the reaction temperature is reduced, and the energy consumption is reduced; and 3) byproducts are few and the yield is high.
Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of N,O-Acetal with Ynamides
Han, Pan,Mao, Zhuo-Ya,Si, Chang-Mei,Zhou, Zhu,Wei, Bang-Guo,Lin, Guo-Qiang
, p. 914 - 923 (2019/01/24)
An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2-c][1,3]oxazin-1-ones has been developed through a nucleophilic addition-cyclization process of N,O-acetal with ynamides. A number of substituted ynamides 8a-8o and 3-silyloxypyrrolidine or piperidine N,O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a-9o, 10a-10m were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, chiral ynamides 14a-14f could also experience this addition-cyclization process to afford products 15a-15f in excellent yields.
Br?nsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: Access to oxygen-bridged tetrahydro-1,4-oxazepines
Zhao, Yingying,Wang, Chunxiang,Hu, Yancheng,Wan, Boshun
supporting information, p. 3963 - 3966 (2018/04/23)
A Br?nsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water is described. This process provides atom-economical access to oxygen-bridged tetrahydro-1,4-oxazepines, where the bridged oxygen atom originates from water. The unique property of the Br?nsted acid shows distinct chemoselectivity from the corresponding gold-catalyzed cycloadditions.
Tf2NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles
Zhao, Yingying,Hu, Yancheng,Wang, Chunxiang,Li, Xincheng,Wan, Boshun
, p. 3935 - 3942 (2017/04/11)
An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol may find applications in pharmaceutical-oriented synthesis.
