Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds?
Green Chemistry Pub Date: 2014-03-27 DOI: 10.1039/C4GC00098F
Abstract
A highly stereoselective organocatalytic Michael addition of aldehydes to trans-β-nitrostyrenes using PEG as a recyclable solvent medium is presented. The scope of this organocatalytic system is demonstrated by the formation of several Michael adducts in good yields and stereoselectivities. Furthermore, applying this new protocol to acetaldehyde, we have disclosed an easy formal synthesis of (R)-pregabalin, (R)-phenibut and (R)-bacoflen with good yields and outstanding enantioselectivities.
Recommended Literature
- [1] Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation Matthew J. Gaunt,Jinquan Yu,Jonathan B. SpencerChem. Commun., 2001, 1844-1845 10.1039/B103066N
- [2] Embedding heteroatoms: an effective approach to create porphyrin-based functional materials Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro OsukaDalton Trans., 2017,46, 13322-13341 10.1039/C7DT02815F
- [3] Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines? Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. MarcosOrg. Biomol. Chem., 2013,11, 6546-6555 10.1039/C3OB41411F
- [4] Excited-state proton-coupled electron transfer within ion pairs? Gerald J. Meyer,Leif Hammarstr?mChem. Sci., 2020,11, 3460-3473 10.1039/C9SC04941J
- [5] Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study? Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander OrlovCatal. Sci. Technol., 2015,5, 2059-2064 10.1039/C4CY01563K
- [6] Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid Marcin Czapla,Jack SimonsPhys. Chem. Chem. Phys., 2018,20, 21739-21745 10.1039/C8CP04007A
- [7] Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents Craig A. Kelly,David R. RosseinskyPhys. Chem. Chem. Phys., 2001,3, 2086-2090 10.1039/B010092G
- [8] Evolution study of photo-synthesized gold nanoparticles by spectral deconvolution model: a quantitative approach Chung-Sung Yang,Mong-Shian Shih,Fang-Yi ChangNew J. Chem., 2006,30, 729-735 10.1039/B516465F
- [9] Etching of glass microchips with supercritical water? Pavel Karásek,Jakub Grym,Michal Roth,Josef Planeta,Franti?ek ForetLab Chip, 2015,15, 311-318 10.1039/C4LC00843J
- [10] Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China? Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing LiFood Funct., 2018,9, 4234-4245 10.1039/C8FO00787J
Journal Name：Green 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)