Catalytic stereoselective cascade reactions of quinols with trifluoromethyl ketones: direct access to CF3-containing 1,3-dioxolanes?
Organic & Biomolecular Chemistry Pub Date: 2016-04-06 DOI: 10.1039/C6OB00281A
Abstract
A general and efficient synthesis of CF3-containing 1,3-dioxolanes using Et3N-catalyzed ketalization/oxa-Michael cascade of quinols with trifluoromethyl ketones is described. The reaction works efficiently under mild reaction conditions and produces the desired products in 68%–95% yields with acceptable diastereoselectivities. In addition, the reaction proceeds smoothly to give the desired product 3a in 92% yield and with high ee (80%) in the presence of a chiral catalyst (DHQ)2PHAL.
Recommended Literature
- [1] An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo PanigrahiRSC Adv., 2017,7, 16319-16331 10.1039/C7RA00366H
- [2] An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system? Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai ZhangRSC Adv., 2014,4, 49995-50002 10.1039/C4RA08740B
- [3] Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode Analyst, 1996,121, 1123-1126 10.1039/AN9962101123
- [4] An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon? Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu MaRSC Adv., 2021,11, 37631-37642 10.1039/D1RA04788D
- [5] An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands? Eric Wimmer,Daniel Cortés-Borda,Solène Brochard,Elvina Barré,Charlotte Truchet,Fran?ois-Xavier FelpinReact. Chem. Eng., 2019,4, 1608-1615 10.1039/C9RE00096H
- [6] Alt-proteins: A promising future 10.1002/fsat.3701_10.x
- [7] An atomistic mechanism for the degradation of perovskite solar cells by trapped charge? Eunhak Lim,Jiyoung Heo,Seong Keun KimNanoscale, 2019,11, 11369-11378 10.1039/C9NR02193K
- [8] An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. KillardAnalyst, 2008,133, 391-399 10.1039/B716154A
- [9] An approach to the structure and vibrational analysis of cis- and trans-3-chlorostyrene through IR/Raman and INS spectroscopies and theoretical ab initio/DFT calculations? J. M. Granadino-Roldán,M. Fernández-Gómez,A. Navarro,T. Pe?a Ruiz,U. A. JayasooriyaPhys. Chem. Chem. Phys., 2004,6, 1133-1143 10.1039/B314243D
- [10] An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid? Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis NayakNew J. Chem., 2019,43, 4867-4877 10.1039/C9NJ00138G
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)