Asymmetric synthesis of chromans via the Friedel–Crafts alkylation–hemiketalization catalysed by an N,N′-dioxide scandium(iii) complex?
Organic Chemistry Frontiers Pub Date: 2017-05-19 DOI: 10.1039/C7QO00323D
Abstract
An enantioselective tandem Friedel–Crafts alkylation–hemiketalization between electron-rich phenols and α,β-unsaturated ketoesters gave a direct approach to chiral 2,3-disubstituted chromans in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex. High enantioselectivities (up to 95% ee), high diastereoselectivities (up to 14?:?1) and high yields (up to 97%) were obtained for a broad range of substrates under mild reaction conditions.
Recommended Literature
- [1] An analysis of the WTC fires using CIB correlations and simple modeling JGQuintiere 10.1177/0734904121989670
- [2] Alternative synthesis of the anti-baldness compound RU58841? RSC Adv., 2014,4, 14143-14148 10.1039/C4RA00332B
- [3] An integrated cathode and solid electrolyte via in situ polymerization with significantly reduced interface resistance? Jialiang Yuan,Ran Dong,Yuan Li,Yang Liu,Zhuo Zheng,Yuxia Liu,Yan Sun,Benhe Zhong,Zhenguo Wu,Xiaodong GuoChem. Commun., 2021,57, 13004-13007 10.1039/D1CC04485K
- [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 artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes? Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce YeAnalyst, 2021,146, 5542-5549 10.1039/D1AN01071A
- [6] Alt-proteins: A promising future 10.1002/fsat.3701_10.x
- [7] An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency? Green Chem., 2017,19, 1268-1277 10.1039/C6GC03280J
- [8] An apparatus for testing water by measurement of its electrical conductivity Analyst, 1912,37, 538-543 10.1039/AN9123700538
- [9] Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. BudaPhys. Chem. Chem. Phys., 2011,13, 10270-10279 10.1039/C1CP20213H
- [10] Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz JaremkoRSC Adv., 2020,10, 215-227 10.1039/C9RA09350H
Journal Name：Organic Chemistry Frontiers
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)