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

Scholarly Works

• 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
• Rombola, M.; Rawal, V. H. Dicyclopentyl Dithiosquarate as an Intermediate for the Synthesis of Thiosquaramides. Organic letters 2018, 20, 514–517. doi:10.1021/acs.orglett.7b03549

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