Asymmetric Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene

Magnus Rueping and Sadiya Raja
Beilstein J. Org. Chem. 2012, 8, 1819–1824. https://doi.org/10.3762/bjoc.8.208

Supporting Information

Supporting Information File 1: Experimental details and characterization of the synthesized compounds.
Format: PDF Size: 2.1 MB Download

Cite the Following Article

Asymmetric Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene
Magnus Rueping and Sadiya Raja
Beilstein J. Org. Chem. 2012, 8, 1819–1824. https://doi.org/10.3762/bjoc.8.208

How to Cite

Rueping, M.; Raja, S. Beilstein J. Org. Chem. 2012, 8, 1819–1824. doi:10.3762/bjoc.8.208

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.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Yaragorla, S.; Pareek, A. Synthetic Organic Chemistry of α-Imino Ketones: A Graphical Review. SynOpen 2024, 8, 265–272. doi:10.1055/s-0040-1720150
  • Liu, Z.; Qian, Q.-C.; Chen, L.-M.; Li, X. B(C6F5)3/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels-Alder Reaction of Imines and Unactivated Dienes. Organic letters 2024, 26, 3247–3251. doi:10.1021/acs.orglett.4c00874
  • Yamashita, Y.; Yasukawa, T.; Saito, Y.; Kobayashi, S. [4+2] Cycloadditions (Normal-Electron-Demand Hetero-Diels–Alder Reaction). Comprehensive Chirality; Elsevier, 2024; pp 288–325. doi:10.1016/b978-0-32-390644-9.00055-x
  • Zheng, J.; Rong, M.; Feng, F.; Zhang, F.; Cheung, C. W.; Ma, J. Organocatalyst‐Controlled Divergent Asymmetric Aza‐Friedel‐Crafts Reactions of Indol‐3‐ones with 1‐ and 2‐Naphthols. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202300204
  • Zhang, W.-H.; Chen, Z.-Y.; Liu, R.-M.; Liu, X.-W.; Pan, B.-W.; Zhou, J.; Zhou, Y.; Tian, Y.-P.; Liu, X.-L. Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions. New Journal of Chemistry 2023, 47, 12296–12303. doi:10.1039/d3nj00901g
  • Nagare, Y. K.; Shah, I. A.; Yadav, J.; Pawar, A. P.; Rangan, K.; Choudhary, R.; Iype, E.; Kumar, I. Electrochemical Oxidative Addition of Nucleophiles on 2-Arylindoles: Synthesis of C2-Heteroquaternary Indolin-3-ones. The Journal of organic chemistry 2022, 87, 15771–15782. doi:10.1021/acs.joc.2c01734
  • Pareek, A.; Singh, G.; Yaragorla, S. Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202200395
  • Yan, J.; Zheng, L.; Wang, J.; Liu, X.; Hu, Y. Indoles Oxidative Ring-Opening/Cyclization Cascade with the 1,2-Diaminoarenes: Direct Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines. The Journal of organic chemistry 2022, 87, 6347–6351. doi:10.1021/acs.joc.1c03120
  • Yadav, J.; Dolas, A. J.; Iype, E.; Rangan, K.; Ohshita, J.; Kumar, D.; Kumar, I. Asymmetric Synthesis of Bridged N-Heterocycles with Tertiary Carbon Center through Barbas Dienamine-Catalysis: Scope and Applications. The Journal of organic chemistry 2021, 86, 17213–17225. doi:10.1021/acs.joc.1c02295
  • Zhao, Q.; Li, Y.; Zhang, Q.-X.; Cheng, J.-P.; Li, X. Catalytic Asymmetric Aza-Diels-Alder Reaction of Ketimines and Unactivated Dienes. Angewandte Chemie (International ed. in English) 2021, 60, 17608–17614. doi:10.1002/anie.202104788
  • Zhao, Q.; Li, Y.; Zhang, Q.; Cheng, J.; Li, X. Catalytic Asymmetric Aza‐Diels–Alder Reaction of Ketimines and Unactivated Dienes. Angewandte Chemie 2021, 133, 17749–17755. doi:10.1002/ange.202104788
  • Vinogradov, M. G.; Turova, O. V.; Zlotin, S. G. Catalytic Asymmetric Aza‐Diels‐Alder Reaction: Pivotal Milestones and Recent Applications to Synthesis of Nitrogen‐Containing Heterocycles. Advanced Synthesis & Catalysis 2021, 363, 1466–1526. doi:10.1002/adsc.202001307
  • Zhou, Z.; Xu, Y.; Zhu, B.; Li, P.; Hu, G.; Yang, F.; Xu, S.; Zhang, X. One-pot synthesis of 3-hydroxy-2-oxindoles via acyloin rearrangements of 2-hydroxy-indolin-3-ones generated in situ from 2-alkynyl arylazides. New Journal of Chemistry 2020, 44, 20303–20307. doi:10.1039/d0nj04588h
  • Li, P.; Zhu, B.; Xu, Y.; Zhou, Z.; Hu, G.; Yang, F.; Xu, S.; Zhang, X. Palladium-catalyzed one-pot cycloaddition reactions of thioureas with 3H-indol-3-ones generated in situ from 2-alkynyl arylazides: rapid and efficient access to imidazoloindolines. Organic Chemistry Frontiers 2020, 7, 3480–3485. doi:10.1039/d0qo00799d
  • Li, P.; Sheng, R.; Zhou, Z.; Hu, G.; Zhang, X. Synthesis of N‐Fused Seven‐Membered Indoline‐3‐ones via a Palladium‐Catalyzed One‐Pot Insertion Reaction from 2‐Alkynyl Arylazides and Cyclic β‐Diketones. European Journal of Organic Chemistry 2020, 2020, 2146–2152. doi:10.1002/ejoc.202000243
  • Fang, S.; Jin, S.; Ma, R.; Lu, T.; Du, D. Asymmetric Synthesis of C2-Quaternary Indolin-3-ones Enabled by N-Heterocyclic Carbene Catalysis. Organic letters 2019, 21, 5211–5214. doi:10.1021/acs.orglett.9b01823
  • Iwanejko, J.; Wojaczyńska, E. Cyclic imines – preparation and application in synthesis. Organic & biomolecular chemistry 2018, 16, 7296–7314. doi:10.1039/c8ob01874j
  • Li, J.-S.; Liu, Y.-J.; Li, S.; Ma, J.-A. Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclic C-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones. Chemical communications (Cambridge, England) 2018, 54, 9151–9154. doi:10.1039/c8cc05125a
  • Cheng, D.-J.; Shao, Y.-D. Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles. Advanced Synthesis & Catalysis 2018, 360, 3614–3642. doi:10.1002/adsc.201800345
  • Guo, S.; Wang, F.; Tao, L.; Zhang, X.; Fan, X. Solvent-Dependent Copper-Catalyzed Indolyl C3-Oxygenation and N1-Cyclization Reactions: Selective Synthesis of 3H-Indol-3-ones and Indolo[1,2-c]quinazolines. The Journal of organic chemistry 2018, 83, 3889–3896. doi:10.1021/acs.joc.8b00231
Other Beilstein-Institut Open Science Activities