All-carbon [3 + 2] cycloaddition in natural product synthesis

Zhuo Wang and Junyang Liu
Beilstein J. Org. Chem. 2020, 16, 3015–3031. https://doi.org/10.3762/bjoc.16.251

Cite the Following Article

All-carbon [3 + 2] cycloaddition in natural product synthesis
Zhuo Wang and Junyang Liu
Beilstein J. Org. Chem. 2020, 16, 3015–3031. https://doi.org/10.3762/bjoc.16.251

How to Cite

Wang, Z.; Liu, J. Beilstein J. Org. Chem. 2020, 16, 3015–3031. doi:10.3762/bjoc.16.251

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: 11.6 MB Download

Citations to This Article

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

Scholarly Works

  • Debnath, S.; Maity, S. Distonic Radical Cations in Visible‐Light‐Driven Cycloadditions. ChemPhotoChem 2025. doi:10.1002/cptc.202500249
  • Zhu, Z.; Tian, P.; Chang, J.; Li, H.; Kang, Y.; Xie, P.; Yao, T.; Zhang, X. Photocatalytic (3+3) cycloaddition of arylaminocyclopropanes with nitrones: highly diastereoselective synthesis of 1,2-oxazinan-6-amine derivatives. Chemical communications (Cambridge, England) 2025. doi:10.1039/d5cc03888j
  • Jana, D.; Noskar, S.; Nandy, M.; Majhi, M.; Bisai, A. Enantioselective Synthesis of the Proposed Structure of (-)-Taiwaniadduct F. Organic letters 2025, 27, 11878–11883. doi:10.1021/acs.orglett.5c03765
  • Karacaoğlu, U. M.; Türkmen, Y. E. Brønsted-Acid-Promoted Diaza-Nazarov Cyclization to Access Tetrasubstituted Pyrazoles. Organic letters 2025, 27, 11094–11099. doi:10.1021/acs.orglett.5c03531
  • de Jesus, I. S.; de Pontes, J. B.; de Carvalho, A. S.; Ferreira, P. G.; de Souza, A. S.; de Carvalho da Silva, F.; Paschoalin, V. M. F.; Futuro, D. O.; Ferreira, V. F. Recent Advances in the Application of Sulfonic Acid Chitosan as Heterogenous Organocatalyst in Organic Reactions. Current Organic Chemistry 2025, 29, 1078–1091. doi:10.2174/0113852728332274241104114316
  • Wang, Y.-Y.; Fu, T.-F.; Hu, X.; Liu, B.; Teng, M.-Y.; Huang, G.-L.; Zhang, L. Metal-Free Visible-Light Excitation of TMSN3 Enables [3 + 2] Cycloaddition of Arylidenecyclopropanes with Olefins. Organic letters 2025, 27, 4095–4100. doi:10.1021/acs.orglett.5c00335
  • Alves, A. J. S.; Silvestre, J. A. D.; Pinho e Melo, T. M. V. D. Continuous Flow Spirocyclization Reactions: Towards Efficient Synthesis of Chiral Spiropenicillanates. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202400689
  • Song, J.-Y.; Sun, X.-Y.; Wang, B.-L.; Zhou, S.-S.; Song, J.-X.; Zhang, B.-H.; Wang, X.-W. COAP-Pd Catalyzed Asymmetric Formal [3+2] Cycloaddition for Optically Active Multistereogenic Spiro Cyclopentane-Indandiones Bearing Cyclic N-Sulfonyl Ketimine Skeletons. Chemistry, an Asian journal 2024, 19, e202400184. doi:10.1002/asia.202400184
  • Qatran Al-Khdhairawi, A. A.; Yuan, T.; Van Hecke, K.; Winne, J. M. Dearomative (3 + 2) Cycloaddition of Indoles for the Stereoselective Assembly of Fully Functionalized Cyclopentanoids. Organic letters 2024, 26, 4077–4081. doi:10.1021/acs.orglett.4c01139
  • Ishihara, J. Progress in Lewis-Acid-Templated Diels-Alder Reactions. Molecules (Basel, Switzerland) 2024, 29, 1187. doi:10.3390/molecules29051187
  • Gupta, K.; Harariya, M. S.; Tyagi, A.; Jindal, G. Overview of Transition Metal Catalyzed Multicomponent Reactions Based on Trapping of Allylic Electrophiles. ChemCatChem 2024, 16. doi:10.1002/cctc.202301215
  • Dhandabani, G. K.; Jeyakannu, P.; Shih, C.-L.; Abraham, A. M.; Senadi, G. C.; Wang, J.-J. A Regioselective [3 + 2] Cycloaddition of Alkynols and Ketones To Access Diverse 1,3-Dioxolane Scaffolds. The Journal of organic chemistry 2023, 89, 719–724. doi:10.1021/acs.joc.3c01820
  • Kowalska, E.; Dyguda, M.; Artelska, A.; Albrecht, A. Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[b]chromenocarbonitrile Derivatives. The Journal of organic chemistry 2023, 88, 16589–16597. doi:10.1021/acs.joc.3c02172
  • Degroote, F.; Denoo, B.; Ryckaert, B.; Callebaut, B.; Van Hecke, K.; Hullaert, J.; Winne, J. M. Dithioallyl cation (3 + 2) cycloadditions under aprotic reaction conditions: rapid access to spiro-fused cyclopentane scaffolds. Organic & biomolecular chemistry 2023, 21, 8117–8124. doi:10.1039/d3ob01273e
  • Wu, W.-Q.; Lin, Y.; Li, Y.; Shi, H. Catalytic Dehydrogenative (3 + 2) Cycloaddition of Alkylbenzenes via π-Coordination. Journal of the American Chemical Society 2023, 145, 9464–9470. doi:10.1021/jacs.3c02900
  • Mao, Y.; Fan, P.; Wang, C. Photocatalyzed Formal All-Carbon [3+2] Cycloaddition of Aromatic Aldehydes with Arylethynyl Silanes. Organic letters 2022, 24, 9413–9418. doi:10.1021/acs.orglett.2c03807
  • Deepthi, A.; Mohan, M.; Balachandran, M. C. Recent Progress on the [3+2] Cycloaddition Route for the Synthesis of All-Carbon Quaternary Stereocentres. SynOpen 2022, 6, 270–285. doi:10.1055/a-1947-3351
  • Hui, C.; Wang, S.; Xu, C. Dinitrogen extrusion from diazene in organic synthesis. Chinese Chemical Letters 2022, 33, 3695–3700. doi:10.1016/j.cclet.2022.03.073
  • Ryckaert, B.; Hullaert, J.; Van Hecke, K.; Winne, J. M. Dearomative (3 + 2) Cycloadditions of Unprotected Indoles. Organic letters 2022, 24, 4119–4123. doi:10.1021/acs.orglett.2c01214
  • Niedbała, P.; Majdecki, M.; Grodek, P.; Jurczak, J. H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters. Molecules (Basel, Switzerland) 2022, 27, 2508. doi:10.3390/molecules27082508

Patents

  • RUGERI BAPTISTE; CHERRY FLORENCE; HOMMET GAËL; MAYER STANISLAS; SCHANN STEPHAN. NOVEL PAR-2 INHIBITORS. WO 2023233033 A1, Dec 7, 2023.
Other Beilstein-Institut Open Science Activities