Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

Scholarly Works

• Karuo, Y.; Hirata, K.; Tarui, A.; Sato, K.; Kawai, K.; Omote, M. Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers. Beilstein Journal of Organic Chemistry 2024, 20, 2691–2703. doi:10.3762/bjoc.20.226
• Saranraj, K.; Raja, K. M. P. Microwave-assisted synthesis of peptidomimetic trans-delta-aminopent-3-enoic acid and its derivatives. New Journal of Chemistry 2024, 48, 16620–16630. doi:10.1039/d4nj02213k
• Zeng, D.; Liu, Z.; Huang, G.; Wang, Y.; Zhu, S. Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes. Nature communications 2024, 15, 7645. doi:10.1038/s41467-024-52054-6
• Sun, H.-L.; Su, M.-X.; Zhang, X.; Qian, Y.-J.; Wan, J.-R.; Si, W.-L.; Sun, Y.-X.; Zhou, X.-Y.; Zhou, H.-P.; Lu, X.-Y. Synthesis of monofluoroalkenes via photocatalyzed decarboxylative and deboronative coupling of α-fluoroacrylic acids with organotrifluoroborates. Tetrahedron 2024, 163, 134166. doi:10.1016/j.tet.2024.134166
• Lu, X.-Y.; Qian, Y.-J.; Sun, H.-L.; Su, M.-X.; Wang, Z.-Z.; Jiang, F.; Zhou, X.-Y.; Sun, Y.-X.; Shi, W.-L.; Wan, J.-R. Photoinduced decarboxylative germylation of α-fluoroacrylic acids: access to germylated monofluoroalkenes. Chemical communications (Cambridge, England) 2024, 60, 6556–6559. doi:10.1039/d4cc02037e
• Kong, L.; Ti, W.; Lin, A.; Yao, H.; Huang, Y.; Li, X. Palladium-Catalyzed Defluorinative Alkylation of gem-Difluoroalkenes with Cyclopropanols: Stereoselective Synthesis of γ-Fluorinated γ,δ-Unsaturated Ketones. Organic letters 2024, 26, 3591–3596. doi:10.1021/acs.orglett.4c01045
• Lu, X.-Y.; Huang, R.; Wang, Z.-Z.; Zhang, X.; Jiang, F.; Yang, G.-X.; Shui, F.-Y.; Su, M.-X.; Sun, Y.-X.; Sun, H.-L. Photoinduced Decarboxylative Difluoroalkylation and Perfluoroalkylation of α-Fluoroacrylic Acids. The Journal of organic chemistry 2024, 89, 6494–6505. doi:10.1021/acs.joc.4c00684
• Lu, X.-Y.; Sun, H.-L.; Su, M.-X.; Zhang, X.; Qian, Y.-J.; Wan, J.-R.; Si, W.-L.; Zhou, H.-P. Synthesis of Monofluoroalkenes Via Photoinduced Decarboxylative and Deboronative Coupling of Α-Fluoroacrylic Acids with Organotrifluoroborates. Elsevier BV 2024. doi:10.2139/ssrn.4862162
• Ahmed, E.-A. M. A.; Zhang, H.; Cao, W.-G.; Gong, T.-J. Palladium-Catalyzed Cross-Coupling of gem-Difluorocyclopropanes with gem-Diborylalkanes for the Synthesis of Boryl-Substituted Fluorinated Alkenes. Organic letters 2023, 25, 9020–9024. doi:10.1021/acs.orglett.3c03626
• Zhang, G.; Li, D.; Xue, F.; Chen, A.; Deng, H. Synthesis of Monofluorocyclohexene via Photocatalytic Defluorinative [4+2] Annulation of gem‐Difluoroalkenes with Unactivated Alkenes. Advanced Synthesis & Catalysis 2023, 365, 4603–4608. doi:10.1002/adsc.202301059
• Li, Y.; Luo, J.; Jiang, Y. C–F bond functionalizations via fluorinated carbenes. Organic Chemistry Frontiers 2023, 10, 5782–5804. doi:10.1039/d3qo01461d
• Keasler, K. T.; Zick, M. E.; Stacy, E. E.; Kim, J.; Lee, J.-H.; Aeindartehran, L.; Runčevski, T.; Milner, P. J. Handling fluorinated gases as solid reagents using metal-organic frameworks. Science (New York, N.Y.) 2023, 381, 1455–1461. doi:10.1126/science.adg8835
• Ferlet, R.; Pucheault, M.; Chabaud, L.; Paquin, J. Metal‐Free Defluoroborylation of 3,3‐Difluoropropenes. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300731
• Yan, Y.; Qian, H.; Lv, L.; Li, Z. Pd-IHept-Catalyzed Ring-Opening of gem-Difluorocyclopropanes with Malonates Via Selective C-C Bond Cleavage: Synthesis of Monofluoroalkenes. The Journal of organic chemistry 2023. doi:10.1021/acs.joc.3c00744
• Yang, H.; Wang, J.; Jin, C.; Li, X.; Xu, X. Au(I)-Catalyzed Regioselective Hydrofluorination of Propargylamines Using Aqueous HF. The Journal of organic chemistry 2023, 88, 12074–12078. doi:10.1021/acs.joc.3c00594
• Lu, X.-Y.; Song, Y.-W.; Shui, F.-Y.; Zhang, X.; Zhou, H.-P.; Yang, G.-X.; Tao, Q.-Q.; Wang, Z.-Z.; Yao, L.-L.; Zhang, J.-L. Stereoselective synthesis of monofluoroalkenyl silanes via copper-catalyzed decarboxylative silylation of α-fluoroacrylic acids. Tetrahedron 2023, 139, 133446. doi:10.1016/j.tet.2023.133446
• Li, X.; Li, Y.; Shan, W.; Wang, Z.; Liu, R.; Zhang, Z.; Li, X.; Shi, D. Nickel-catalyzed stereoselective reductive cross-coupling of gem-difluoroalkenes with alkenyl electrophiles. Chemical communications (Cambridge, England) 2023, 59, 6893–6896. doi:10.1039/d3cc01551c
• Arcoria, P. J.; Etzkorn, F. A. A fluoro-alkene mimic of Gly-trans-Pro produces a stable collagen triple helix. Organic & biomolecular chemistry 2023, 21, 4039–4051. doi:10.1039/d3ob00110e
• Li, Z.; Zhang, Y.; Zhang, Y.; He, X.; Shen, X. Diastereoselective Synthesis of Monofluorocyclohexenes through Photocatalyzed Cascade Cyclization of gem‐Difluoroalkenes and α,β‐Unsaturated Carbonyl Compounds. Angewandte Chemie 2023, 135. doi:10.1002/ange.202303218
• Li, Z.; Zhang, Y.; Zhang, Y.; He, X.; Shen, X. Diastereoselective Synthesis of Monofluorocyclohexenes through Photocatalyzed Cascade Cyclization of gem-Difluoroalkenes and α,β-Unsaturated Carbonyl Compounds. Angewandte Chemie (International ed. in English) 2023, 62, e202303218. doi:10.1002/anie.202303218

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