Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes?
Organic & Biomolecular Chemistry Pub Date: 2018-10-10 DOI: 10.1039/C8OB02063A
Abstract
A modular, stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki–Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally occurring kinase inhibitor BE-23372M.
Recommended Literature
- [1] Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid Marcin Czapla,Jack SimonsPhys. Chem. Chem. Phys., 2018,20, 21739-21745 10.1039/C8CP04007A
- [2] Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage? M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. KaskelJ. Mater. Chem. A, 2015,3, 17983-17990 10.1039/C5TA03730A
- [3] Dissociation of large gaseous serine clusters produces abundant protonated serine octamer Jacob S. Jordan,Evan R. WilliamsAnalyst, 2021,146, 2617-2625 10.1039/D1AN00273B
- [4] Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals? Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael HardyAnalyst, 2019,144, 4194-4203 10.1039/C9AN00468H
- [5] Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials? Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-GarayoaRSC Adv., 2017,7, 24133-24139 10.1039/C7RA03845C
- [6] Establishing new scaling relations on two-dimensional MXenes for CO2 electroreduction? Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei SehJ. Mater. Chem. A, 2018,6, 21885-21890 10.1039/C8TA06567E
- [7] Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces? Shintaro Takata,Yoshihiro MiuraPhys. Chem. Chem. Phys., 2014,16, 24784-24789 10.1039/C4CP03280B
- [8] Emerging enantiomeric resolution materials with homochiral nano-fabrications Ji-Ping WeiNanoscale, 2015,7, 11815-11832 10.1039/C5NR03048J
- [9] Excitation energies from ground-state density-functionals by means of generator coordinates A. B. F. da Silva,K. CapellePhys. Chem. Chem. Phys., 2009,11, 4564-4569 10.1039/B902529D
- [10] Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR? Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing XiaNanoscale, 2020,12, 20456-20466 10.1039/D0NR04995F
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)