Enantioselective Pd-catalyzed tandem allylic alkylation reaction using monodentate phosphoramidite ligands for the formal total synthesis of huperzine A??
Organic Chemistry Frontiers Pub Date: 2014-08-20 DOI: 10.1039/C4QO00180J
Abstract
A small library of fine-tunable monodentate phosphoramidite (MPN) ligands was found useful in selecting a highly efficient chiral ligand for the enantioselective Pd-catalyzed tandem allylic alkylation reaction. The reaction gave a critical tricyclic key intermediate with high enantiopurity for the formal total synthesis of (?)-huperzine A, a Lycopodium alkaloid derived from the club moss Huperzia serrata that possesses potent inhibitory activity against acetylcholine esterase (ACHe).
Recommended Literature
- [1] Enantiomeric two-fold interpenetrated 3D zinc(ii) coordination networks as a catalytic platform: significant difference between water within the cage and trace water in transesterification? Eunkyung Choi,Minjoo Ryu,Haeri Lee,Ok-Sang JungDalton Trans., 2017,46, 4595-4601 10.1039/C7DT00217C
- [2] Exfoliation of transition-metal dichalcogenides using ATP in aqueous solution? Xinyi Liu,Huan Chen,Jing Lin,Yi Li,Liangqia GuoChem. Commun., 2019,55, 2972-2975 10.1039/C8CC10259G
- [3] Distribution and ecological risk assessment of typical antibiotics in the surface waters of seven major rivers, China? Environ. Sci.: Processes Impacts, 2021,23, 1088-1100 10.1039/D1EM00079A
- [4] 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
- [5] Distinctive size effects of Pt nanoparticles immobilized on Fe3O4@PPy used as an efficient recyclable catalyst for benzylic alcohol aerobic oxidation and hydrogenation reduction of nitroaromatics Yu Long,Bing Yuan,Jianrui Niu,Xin Tong,Jiantai MaNew J. Chem., 2015,39, 1179-1185 10.1039/C4NJ01869A
- [6] Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field XuxinCheng,XiaomingChen,PengyuanFan 10.1007/s10832-022-00283-w
- [7] Expanding nanoparticle multifunctionality: size-selected cargo release and multiple logic operations? Danlei XiangNanoscale, 2021,13, 5497-5506 10.1039/D1NR00642H
- [8] Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-MoralesCrystEngComm, 2013,15, 2206-2212 10.1039/C2CE26556G
- [9] Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat VeisiNew J. Chem., 2018,42, 1757-1761 10.1039/C7NJ02513K
- [10] Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario GiordanoAnalyst, 2018,143, 4674-4683 10.1039/C8AN00093J
Journal Name：Organic Chemistry Frontiers
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)