Reactive resin facilitated preparation of an enantiopure fluorobicycloketone
Organic & Biomolecular Chemistry Pub Date: 2003-11-20 DOI: 10.1039/B312180C
Abstract
A facile preparation of enantiopure ethyl (1S,5S,6S)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate 1 is described. The key feature of the synthesis involves copper-catalyzed enantioselective intramolecular cyclopropanation of a diazoketone to form endo-fluorocyclopropane 1 in a single operation. Removal of a problematic chloroketone impurity using a reactive resin treatment enabled a high throughput enantiopurity upgrade by chiral HPLC. The development of a scalable synthesis of 1 is presented, including details of the selection of catalyst and ligand optimization, incorporation of a reactive resin treatment and selection of chiral HPLC media and conditions.
Recommended Literature
- [1] Dissociative dynamics of O2 on Ag(110)? Ivor Lon?ari?Phys. Chem. Chem. Phys., 2015,17, 9436-9445 10.1039/C4CP05900J
- [2] Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process? Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying ChenJ. Mater. Chem. A, 2014,2, 18831-18837 10.1039/C4TA03994G
- [3] Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization. LarsBanko,AlfredLudwig 10.1021/acscombsci.0c00057
- [4] Dissociation of large gaseous serine clusters produces abundant protonated serine octamer Jacob S. Jordan,Evan R. WilliamsAnalyst, 2021,146, 2617-2625 10.1039/D1AN00273B
- [5] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [6] 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
- [7] 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
- [8] Emulsion technologies for multicellular tumour spheroid radiation assays? Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele ZagnoniAnalyst, 2016,141, 100-110 10.1039/C5AN01382H
- [9] Exciplex emission from the mixed dimer of naphthalene and 2-cyanonaphthalene in a supersonic jet Aloke Das,K. K. Mahato,Chayan K. Nandi,Tapas Chakraborty,Shridhar R. Gadre,Nikhil A. GokhalePhys. Chem. Chem. Phys., 2002,4, 2162-2168 10.1039/B200124C
- [10] Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals? Shojiro Kimura,Tetsuro KusamotoChem. Commun., 2020,56, 11195-11198 10.1039/D0CC04830E
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.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)