Supporting Information
| Supporting Information File 1: Experimental details, ORTEP drawings of 1a, 1b, 1d–1f, theoretical calculations of C1–C6, and NMR spectra of all new compounds and C1–C6. | ||
| Format: PDF | Size: 11.2 MB | Download |
|
Supporting Information File 2:
X-ray structure analysis data for 1a (CCDC-1813600), 1b (CCDC-1813582), 1d (CCDC-1813594), 1e (CCDC-1813595), 1f (CCDC-1813596). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
X-ray analysis of 1a–f. |
||
| Format: CIF | Size: 4.5 MB | Download |
Cite the Following Article
Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations
Koichi Mitsudo, Junya Yamamoto, Tomoya Akagi, Atsuhiro Yamashita, Masahiro Haisa, Kazuki Yoshioka, Hiroki Mandai, Koji Ueoka, Christian Hempel, Jun-ichi Yoshida and Seiji Suga
Beilstein J. Org. Chem. 2018, 14, 1192–1202.
https://doi.org/10.3762/bjoc.14.100
How to Cite
Mitsudo, K.; Yamamoto, J.; Akagi, T.; Yamashita, A.; Haisa, M.; Yoshioka, K.; Mandai, H.; Ueoka, K.; Hempel, C.; Yoshida, J.-i.; Suga, S. Beilstein J. Org. Chem. 2018, 14, 1192–1202. doi:10.3762/bjoc.14.100
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Presentation Graphic
| Picture with graphical abstract, title and authors for social media postings and presentations. | ||
| Format: PNG | Size: 182.5 KB | Download |
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Phillips, R. C.; Chu, J. C. K.; Rafaniello, A. A.; Gaunt, M. J. Selective endo-Cyclic α-Functionalization of Saturated N-Alkyl Piperidines. The Journal of organic chemistry 2025, 90, 12226–12239. doi:10.1021/acs.joc.5c01742
- MATSUMOTO, K.; HAMASAKI, K.; YAMANAKA, R.; MATSUMOTO, K. Paired Electrochemical Synthesis between Cation Pooled Iminium Ion and In Situ Formed Allylsilanes Using Electrochemical Cell that Allows Solution Transfer. Electrochemistry 2025, 93, 37007. doi:10.5796/electrochemistry.25-00038
- Novaes, L. F. T.; Ho, J. S. K.; Mao, K.; Villemure, E.; Terrett, J. A.; Lin, S. α,β-Desaturation and Formal β-C(sp3)-H Fluorination of N-Substituted Amines: A Late-Stage Functionalization Strategy Enabled by Electrochemistry. Journal of the American Chemical Society 2024, 146, 22982–22992. doi:10.1021/jacs.4c02548
- Okamoto, K.; Chiba, K. Electrosynthesis of Artificial Peptides and Nucleosides via the Nitromethane–Lithium Perchlorate Electrolyte System: A Review. ChemElectroChem 2023, 11. doi:10.1002/celc.202300493
- Mitsudo, K.; Inoue, H.; Niki, Y.; Sato, E.; Suga, S. Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility. Beilstein journal of organic chemistry 2022, 18, 1055–1061. doi:10.3762/bjoc.18.107
- Takumi, M.; Sakaue, H.; Shibasaki, D.; Nagaki, A. Rapid access to organic triflates based on flash generation of unstable sulfonium triflates in flow. Chemical communications (Cambridge, England) 2022, 58, 8344–8347. doi:10.1039/d2cc02344j
- Takumi, M.; Sakaue, H.; Nagaki, A. Flash Electrochemical Approach to Carbocations. Angewandte Chemie (International ed. in English) 2022, 61, e202116177. doi:10.1002/anie.202116177
- Novaes, L. F. T.; Ho, J. S. K.; Mao, K.; Liu, K.; Tanwar, M.; Neurock, M.; Villemure, E.; Terrett, J. A.; Lin, S. Exploring Electrochemical C(sp3)-H Oxidation for the Late-Stage Methylation of Complex Molecules. Journal of the American Chemical Society 2022, 144, 1187–1197. doi:10.1021/jacs.1c09412
- Takumi, M.; Sakaue, H.; Nagaki, A. Flash Electrochemical Approach to Carbocations. Angewandte Chemie 2022, 134. doi:10.1002/ange.202116177
- Merx, J.; Houthuijs, K. J.; Elferink, H.; Witlox, E.; Mecinović, J.; Oomens, J.; Martens, J.; Boltje, T. J.; Rutjes, F. P. J. T. Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 28, e202104078. doi:10.1002/chem.202104078
- Dutta, S.; Li, B.; Rickertsen, D. R. L.; Valles, D. A.; Seidel, D. C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods. SynOpen (2017) 2021, 05, 173–228. doi:10.1055/s-0040-1706051
- Kwok, T.; Hoff, O.; Armstrong, R. J.; Donohoe, T. J. Control of Absolute Stereochemistry in Transition-Metal-Catalysed Hydrogen-Borrowing Reactions. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 12912–12926. doi:10.1002/chem.202001253
- Mitsudo, K.; Matsuo, R.; Yonezawa, T.; Inoue, H.; Mandai, H.; Suga, S. Electrochemical Synthesis of Thienoacene Derivatives: Transition-Metal-Free Dehydrogenative C-S Coupling Promoted by a Halogen Mediator. Angewandte Chemie (International ed. in English) 2020, 59, 7803–7807. doi:10.1002/anie.202001149
- Mitsudo, K.; Matsuo, R.; Yonezawa, T.; Inoue, H.; Mandai, H.; Suga, S. Electrochemical Synthesis of Thienoacene Derivatives: Transition‐Metal‐Free Dehydrogenative C−S Coupling Promoted by a Halogen Mediator. Angewandte Chemie 2020, 132, 7877–7881. doi:10.1002/ange.202001149
- Chamberlain, A. E. R.; Paterson, K. J.; Armstrong, R. J.; Twin, H.; Donohoe, T. J. A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles. Chemical communications (Cambridge, England) 2020, 56, 3563–3566. doi:10.1039/d0cc00903b
- Ashikari, Y.; Saito, K.; Nokami, T.; Yoshida, J.-i.; Nagaki, A. Oxo‐Thiolation of Cationically Polymerizable Alkenes Using Flow Microreactors. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 15239–15243. doi:10.1002/chem.201903426
- Eskici, M.; Karanfil, A. Stereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidates. Tetrahedron 2019, 75, 1214–1222. doi:10.1016/j.tet.2019.01.030