Enamine-mediated Mannich reaction of cyclic N,O-acetals and amido acetals: the multigram synthesis of pyrrolidine alkaloid precursors?
Organic & Biomolecular Chemistry Pub Date: 2022-08-25 DOI: 10.1039/D2OB01276F
Abstract
The cooperative L-proline/Br?nsted acid/base promoted reaction of 2-ethoxypyrrolidines or N-substituted 4,4-diethoxybutan-1-amines with methyl(alkyl/aryl)ketones for the synthesis of 2-(acylmethylene)pyrrolidine derivatives is reported. The key features of the developed protocol are gram-scale synthesis of the target compounds, easily available starting materials, operational simplicity and usage of non-expensive reagents.
Recommended Literature
- [1] Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials? Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-GarayoaRSC Adv., 2017,7, 24133-24139 10.1039/C7RA03845C
- [2] Excellent humidity sensor based on ultrathin HKUST-1 nanosheets? Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu ChenRSC Adv., 2021,11, 192-197 10.1039/D0RA08354B
- [3] Establishing new scaling relations on two-dimensional MXenes for CO2 electroreduction? Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei SehJ. Mater. Chem. A, 2018,6, 21885-21890 10.1039/C8TA06567E
- [4] Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces? Shintaro Takata,Yoshihiro MiuraPhys. Chem. Chem. Phys., 2014,16, 24784-24789 10.1039/C4CP03280B
- [5] Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination? Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. SharadaChem. Commun., 2022,58, 1406-1409 10.1039/D1CC06097J
- [6] 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
- [7] Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer? Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun CaoRSC Adv., 2016,6, 42109-42119 10.1039/C6RA05236C
- [8] Excimer–monomer switch: a reaction-based approach for selective detection of fluoride? Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi CaoAnalyst, 2014,139, 3588-3592 10.1039/C4AN00522H
- [9] Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides? Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. MasonEnviron. Sci.: Nano, 2020,7, 1642-1651 10.1039/C9EN01304K
- [10] Excellent kinetics of single-phase Gd-doped ceria fuel electrodes in solid oxide cells? Andreas Nenning,Manuel Holzmann,Jürgen Fleig,Alexander K. OpitzMater. Adv., 2021,2, 5422-5431 10.1039/D1MA00202C
Journal Name：Organic & Biomolecular 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)