Synthesis of highly substituted 2-spiropiperidines?
Organic & Biomolecular Chemistry Pub Date: 2018-07-30 DOI: 10.1039/C8OB01272E
Abstract
2-Spiropiperidines are a highly desirable, yet under represented structure in drug discovery. 2-Spiropiperidines were synthesised in either a two-pot or one-pot reaction. In the two-pot reaction, the addition of a Weiler dianion to N-Boc imines, followed by deprotection and in situ condensation with a cyclic ketone generated functionalised 2-spiropiperidines in good to excellent yields. In the one-pot reaction, the addition of Chan's diene to N-Boc imines under Maitland–Japp conditions, followed by the addition of sodium bicarbonate and a cyclic ketone formed functionalised 2-spiropiperidines in moderate to good yields.
Recommended Literature
- [1] Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele PeregoRSC Adv., 2016,6, 3617-3622 10.1039/C5RA26710B
- [2] 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
- [3] Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component? Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. TsukerblatDalton Trans., 2017,46, 7540-7548 10.1039/C7DT01236E
- [4] Emergence of microfluidic wearable technologies Joo Chuan Yeo,KenryLab Chip, 2016,16, 4082-4090 10.1039/C6LC00926C
- [5] Evolution of dealloying induced strain in nanoporous gold crystals? Ross Harder,David C. Dunand,Ian McNultyNanoscale, 2017,9, 5686-5693 10.1039/C6NR09635B
- [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] Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4? Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di MaRSC Adv., 2018,8, 19353-19361 10.1039/C8RA02762E
- [8] Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra KumarRSC Adv., 2016,6, 94731-94738 10.1039/C6RA18729C
- [9] Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration? Ziyang Deng,Changwei Chen,Sunliang CuiRSC Adv., 2016,6, 93753-93755 10.1039/C6RA20007A
- [10] Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications Partha Laskar,Christine DufèsNanoscale Adv., 2021,3, 6007-6026 10.1039/D1NA00536G
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)